Acyl-mercapto-triazolyl derivatives and the use thereof as microbicides

ABSTRACT

PCT No. PCT/EP97/01997 Sec. 371 Date Oct. 27, 1998 Sec. 102(e) Date Oct. 27, 1998 PCT Filed Apr. 21, 1997 PCT Pub. No. WO97/42178 PCT Pub. Date Nov. 13, 1997The present invention provides the composition for novel acyl-mercapto-triazolyl derivatives, and the acid addition salts and metal salt complexes thereof; a process for their preparation; and a method for their use as microbicides.

The present invention relates to novel acyl-mercapto-triazolylderivatives, to a process for their preparation and to their use asmicrobicides.

It is already known that numerous triazolyl derivatives have fungicidalproperties (cf. EP-A 0 015 756, EP-A 0 040 345, EP-A 0 052 424, EP-A 0061 835, EP-A 0 297 345. EP-A 0 094 564, EP-A 0 196 038, EP-A 0 267 778,EP-A 0 378 953Ad, EP-A 0 044 605. EP-A 0 069 442, EP-A 0 055 833, EP-A 0301 393, DE-A 2 324 010, DE-A 2 737 489, DE-A 2 551 560, EP-A 0 065 485,DE-A 2 735 872, EP-A 0 234 242, DE-A 2 201 063, EP-A 0 145 294 and DE-A3) 721 786). The activity of these substances is good, but in some casesleaves something to be desired at low application rates.

This invention, accordingly, provides novel acyl-mercapto-triazolylderivatives of the formula ##STR1## in which R represents alkyl,halogenoalkyl, optionally substituted aryl, optionally, substitutedaralkyl, alkoxy, alkylamino or optionally substituted arylamino and

R¹ represents a radical of the formula ##STR2## R² and R³ are identicalor different and each represent optionally substituted alkyl, optionallysubstituted alkenyl, optionally substituted cycloalkyl, optionallysubstituted aralkyl, optionally substituted aralkenyl, optionallysubstituted aroxyalkyl, optionally substituted aryl or optionallysubstituted heteroaryl,

or

R¹ represents a radical of the formula ##STR3## R⁴ represents alkylhaving 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and1 to 5 halogen atoms, optionally halogen-substituted cycloalkyl having 3to 7 carbon atoms, naphthyl or phenyl which is optionally mono- totrisubstituted bid identical or different substituents selected from thegroup consisting of halogen, nitro, phenyl, phenoxy alkyl having 1 to 4carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4carbon atoms and 1 to 5 halogen atoms and halogenoalkylthio having 1 to4 carbon atoms and 1 to 5 halogen atoms, and

R⁵ represents phenyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5halogen atoms and halogenoalkylthio having 1 to 4 carbon atoms and 1 to5 halogen atoms,

or

R¹ represents a radical of the formula ##STR4## R⁶ and R⁷ independentlyof one another each represent hydrogen or alkyl having 1 to 6 carbonatoms,

X¹ represents halogen, alkyl having 1 to 5 carbon atoms, alkoxy having 1to 4 carbon atoms, phenyl, phenoxy, halogenoalkyl having 1 to 4 carbonatoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbonatoms and 1 to 5 halogen atoms or represents halogenoalkylthio having 1to 4 carbon atoms and 1 to 5 halogen atoms, and

m represents the numbers 0. 1 or 2,

or

R¹ represents a radical of the formula ##STR5## R⁸ and R⁹ independentlyof one another each represent hydrogen or alkyl having 1 to 6 carbonatoms,

X² represents halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms,alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbonatoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbonatoms and 1 to 5 halogen atoms or phenyl,

n represents the numbers 0 or 1 and

p represents the numbers 0, 1 or 2,

or

R¹ represents a radical of the formula ##STR6## R¹⁰ represents alkylhaving 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and1 to 5 halogen atoms, cycloalkyl having 3 to 6 carbon atoms which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, optionally substituted aryl or represents optionally substitutedaralkyl,

or

R¹ represents a radical of the formula ##STR7## R¹¹ represents hydrogen,alkyl or optionally substituted cycloalkyl, X³ represents halogen, alkylhaving 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthiohaving 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to5 halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5halogen atoms, phenyl which is optionally substituted by halogen and/oralkyl having 1 to 4 carbon atoms or represents phenoxy which isoptionally substituted by halo-en and/or alkyl having 1 to 4 carbonatoms,

q represents the numbers 0. 1. 2 or 3 and

Y¹ represents an oxygen atom, a CH₂ group or a direct bond,

or

R¹ represents a radical of the formula ##STR8## R¹² represents alkylhaving 1 to 6 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and1 to 5 halogen atoms, cycloalkyl having 3 to 7 carbon atoms which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkylmoiety and 1 to 4 carbon atoms in the alkyl moiety, optionallyhalogen-substituted phenyl or represents optionally halogen-substitutedbenzyl,

X⁴ represents halogen, nitro, alkyl having 1 to 4 carbon atoms, alkoxyhaving 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms,halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms,halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms,phenyl which is optionally substituted by halogen and/or alkyl having 1to 4 carbon atoms, or represents phenoxy which is optionally substitutedby halogen and/or alkyl having 1 to 4 carbon atoms,

r represents the numbers 0. 1. 2 or 3 and

Y² represents an oxygen atom or represents a CH₂ group,

or

R¹ represents a radical of the formula ##STR9## A represents alkanediylhaving 2 or 3 carbon atoms which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms,

X¹ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms

and

s represents the numbers 0, 1, 2 or 3,

or

R¹ represents a radical of the formula ##STR10## R¹³ represents alkylhaving 1 to 10 carbon atoms, halogenoalkyl having 1 to 6 carbon atomsand 1 to 5 halogen atoms, fluoroalkoxyalkyl having 1 to 4 carbon atomsin the fluoroalkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety,cycloalkyl having 3 to 7 carbon atoms which is optionally substituted byhalogen and/or alkyl having 1 to 4 carbon atoms, cycloalkylalkyl having3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms inthe alkyl moiety, optionally halogen-substituted phenyl or representsoptionally halogen-substituted phenylalkyl having 1 to 4 carbon atoms inthe alkyl moiety,

X⁶ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms, and

t represents the numbers 0, 1, 2 or 3,

or

R¹ represents a radical of the formula ##STR11## R¹⁴ represents alkylhaving 1 to 6 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and1 to 5 halogen atoms, cycloalkyl having 3 to 7 carbon atoms which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkylmoiety and 1 to 4 carbon atoms in the alkyl moiety, optionallyhalogen-substituted phenyl or represents optionally halogen-substitutedbenzyl,

X⁷ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms,

u represents the numbers 0, 1. 2 or 3 and

Y³ represents an oxygen atom or represents a CH₂ group,

or

R¹ represents a radical of the formula ##STR12## R¹⁵ represents alkylhaving 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and1 to 5 halogen atoms, optionally substituted aryl or representsoptionally substituted aralkyl,

X⁸ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms and

v represents the numbers 0, 1, 2 or 3,

and acid addition salts and metal salt complexes thereof.

A large number of the substances according to the invention contain oneor more asymmetrically substituted carbon atoms. They may therefore beobtained in the form of optical isomers. The present invention relatesboth to the individual isomers and to mixtures thereof.

Furthermore, it has been found that acyl-mercapto-triazolyl derivativesof the formula (I) and acid addition salts and metal salt complexesthereof are obtained when mercapto-triazoles of the formula ##STR13## inwhich R¹ is as defined above

are either

a) reacted with acyl halides of the formula

    R.sup.16 --CO--Hal                                         (III)

in which

R¹⁶ represents alkyl, halogenoalkyl, optionally substituted aryl oroptionally substituted aralkyl and

Hal represents chlorine or bromine

if appropriate in the presence of an acid binder and if appropriate inthe presence of a diluent,

or

b) reacted with halogenoformates of the formula ##STR14## in which R¹⁷represents alkyl and

Hal¹ represents chlorine or bromine,

if appropriate in the presence of an acid binder and if appropriate inthe presence of a diluent,

or

c) reacted with isocyanates of the formula

    R.sup.18 --N═C═O                                   (V)

in which

R¹⁸ represents alkyl or represents optionally substituted aryl,

if appropriate in the presence of a catalyst and if appropriate in thepresence of a diluent,

and, if appropriate, an acid or a metal salt is subsequently added tothe resulting compounds of the formula (I).

Finally, it has been found that the novel acyl-mercapto-triazolylderivatives of the formula (I) and acid addition salts and metal saltcomplexes thereof have very good microbicidal properties and can be usedboth in crop protection and in the protection of materials forcontrolling undesirable microorganisms.

Surprisingly, the substances according to the invention have bettermicrobicidal activity, in particular fungicidal activity, than theconstitutionally most similar compounds of the same direction of action.

The formula (I) provides a general definition of theacyl-mercapto-triazolyl derivatives according to the invention.

R preferably represents straight-chain or branched alkyl having 1 to 8carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6carbon atoms and 1 to 5 identical or different halogen atoms, phenylwhich is optionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen and alkylhaving 1 to 4 carbon atoms, phenylalkyl having 1 to 4 carbon atoms inthe alkyl moiety which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen and alkyl having 1 to 4 carbon atoms, straight-chain orbranched alkoxy having 1 to 12 carbon atoms, straight-chain or branchedalkylamino having 1 to 14 carbon atoms or represents phenylamino whichis optionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen and alkylhaving 1 to 4 carbon atoms.

R¹ preferably represents a radical of the formula ##STR15## R²preferably represents straight-chain or branched alkyl having 1 to 6carbon atoms, it being possible for these radicals to be mono- totetrasubstituted by identical or different substituents selected fromthe a group consisting of halogen, alkoxy having 1 to 4 carbon atoms,alkoximino having 1 to 4 carbon atoms in the alkoxy moiety andcycloalkyl having 3 to 7 carbon atoms,

or

preferably represents straight-chain or branched alkenyl having 2 to 6carbon atoms, it being possible for each of these radicals to be mono-to trisubstituted by identical or different substituents selected fromthe group consisting of halogen, alkoxy having 1 to 4 carbon atoms andcycloalkyl having 3 to 7 carbon atoms,

or

preferably represents cycloalkyl having 3 to 7 carbon atoms, it beingpossible for each of these radicals to be mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, cyano and alkyl having 1 to 4 carbon atoms,

or

preferably represents aralkyl having 6 to 10 carbon atoms in the arylmoiety and 1 to 4 carbon atoms in the straight-chain or branched alkylmoiety, it being possible for each of the aryl moieties to be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxyhaving 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1to 5 identical or different halogen atoms, halogenoalkylthio having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonylhaving 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety, nitro and cyano,

or

preferably represents aralkenyl having 6 to 10 carbon atoms in the arylmoiety and 2 to 4 carbon atoms in the alkenyl moiety, it being possiblefor each of the aryl moieties to be mono- to trisubstituted by identicalor different substituents selected from the group consisting of halogen,alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms,alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbonatoms and 1 to 5 identical or different halogen atoms, halogenoalkoxyhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identicalor different halogen atoms, cycloalkyl having 3 to 7 carbon atoms,phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxymoiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moietyand 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano,

or

preferably represents aroxyalkyl having 6 to 10 carbon atoms in the arylmoiety and 1 to 4 carbon atoms in the straight-chain or branchedoxyalkyl moiety, it being possible for each of the aryl moieties to bemono- to trisubstituted by identical or different substituents selectedfrom the group consisting of halogen, alkyl having 1 to 4 carbon atoms,alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1to 5 identical or different halogen atoms, halogenoalkylthio having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonylhaving 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety, nitro and cyano,

or

preferably represents aryl having 6 to 10 carbon atoms, it beingpossible for each of these radicals to be mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand cyano,

or

preferably represents an optionally benzo-fused five- or six-memberedheteroaromatic radical having 1 to 3 hetero atoms, such as nitrogen,sulphur and/or oxygen, it being possible for each of these radicals tobe mono- to trisubstituted by identical or different substituentsselected from the group consisting of halogen, alkyl having 1 to 4carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms, hydroxyalkinylhaving 3 to 8 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthiohaving 1 or 2 carbon atoms, halogenoalkyl, halogenoalkoxy andhalogenoalkylthio having in each case 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms such as fluorine or chlorine atoms,formyl, dialkoxymethyl having 1 or 2 carbon atoms in each alkoxy group,acyl having 2 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 3 carbon atoms in the alkyl moiety, nitroand cyano, and

R³ preferably represents straight-chain or branched alkyl having 1 to 6carbon atoms, it being possible for these radicals to be mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of halogen, alkoxy having 1 to 4 carbon atoms,alkoximino having 1 to 4 carbon atoms in the alkoxy moiety andcycloalkyl having 3 to 7 carbon atoms,

or

preferably represents straight-chain or branched alkenyl having 2 to 6carbon atoms, it being possible for each of these radicals to be mono-to trisubstituted by identical or different substituents selected fromthe group consisting of halogen, alkoxy having 1 to 4 carbon atoms andcycloalkyl having 3 to 7 carbon atoms,

or

preferably represents cycloalkyl having 3 to 7 carbon atoms, it beingpossible for each of these radicals to be mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, cyano and alkyl having 1 to 4 carbon atoms,

or

preferably represents aralkyl having 6 to 10 carbon atoms in the arylmoiety and 1 to 4 carbon atoms in the straight-chain or branched alkylmoiety, it being possible for each of the aryl moieties to be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxyhaving 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1to 5 identical or different halogen atoms, halogenoalkylthio having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonylhaving 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety, nitro and cyano,

or

preferably represents aralkenyl having 6 to 10 carbon atoms in the arylmoiety and 2 to 4 carbon atoms in the alkenyl moiety, it being possiblefor each of the aryl moieties to be mono- to trisubstituted by identicalor different substituents selected from the group consisting of halogen,alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms,alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbonatoms and 1 to 5 identical or different halogen atoms, halogenoalkoxyhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identicalor different halogen atoms, cycloalkyl having 3 to 7 carbon atoms,phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxymoiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moietyand 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano,

or

preferably represents aroxyalkyl having 6 to 10 carbon atoms in the arylmoiety and 1 to 4 carbon atoms in the straight-chain or branchedoxyalkyl moiety, it being possible for each of the aryl moieties to bemono- to trisubstituted by identical or different substituents selectedfrom the group consisting of halogen, alkyl having 1 to 4 carbon atoms,alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1to 5 identical or different halogen atoms, halogenoalkylthio having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonylhaving 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety, nitro and cyano,

or

preferably represents aryl having 6 to 10 carbon atoms, it beingpossible for each of these radicals to be mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand cyano,

or

preferably represents an optionally benzo-fused five- or six-memberedheteroaromatic radical having 1 to 3 hetero atoms, such as nitrogen,sulphur and/or oxygen, it being possible for each of these radicals tobe mono- to trisubstituted by identical or different substituentsselected from the group consisting of halogen, alkyl having 1 to 4carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms, hydroxyalkinylhaving 3 to 8 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthiohaving 1 or 2 carbon atoms, halogenoalkyl, halogenoalkoxy andhalogenoalkylthio having in each case 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms, such as fluorine or chlorineatoms, formyl, dialkoxymethyl having 1 or 2 carbon atoms in each alkoxygroup, acyl having 2 to 4 carbon atoms, alkoxycarbonyl having 1 to 4carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbonatoms in the alkoxy moiety and 1 to 3 carbon atoms in the alkyl moiety,nitro and cyano,

R¹ furthermore preferably represents a radical of the formula ##STR16##R⁴ preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl,sec-butyl, isobutyl, tert-butyl, fluoro-tert-butyl, difluoro-tert-butyl,cycloalkyl having 3 to 6 carbon atoms which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine and bromine, represents naphthylor represents phenyl which may be mono- to trisubstituted by identicalor different substituents selected from the group consisting offluorine, chlorine, bromine, nitro, phenyl, phenoxy, methyl, ethyl,tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl,difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxyand trifluoromethylthio, and

R⁵ preferably represents phenyl which may be mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl,methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl,difluorochloromethyl, trifluoromethoxy, difluoromethoxy andtrifluoromethylthio.

R¹ furthermore preferably represents a radical of the formula ##STR17##

R⁶ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

R⁷ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

X¹ preferably represents fluorine, chlorine, bromine, methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy,ethoxy, phenyl, phenoxy, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy or trifluoromethylthio and

m also preferably represents the numbers 0, 1 or 2,

where X¹ may represent identical or different radicals if m represents2.

R¹ furthermore preferably represents a radical of the formula ##STR18##R⁸ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

R⁹ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

X² preferably represents fluorine, chlorine, bromine, cyano, nitro,methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl,tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl,difluoromethyl, trichloromethoxy, trifluoromethoxy, difluoromethoxy,difluorochloromethoxy or phenyl,

n also preferably represents the numbers 0 or 1 and

p also preferably represents the numbers 0, 1 or 2.

where X² may represent identical or different radicals if p represents2.

R¹ furthermore preferably represents a radical of the formula ##STR19##R¹⁰ preferably represents straight-chain or branched alkyl having 1 to 4carbon atoms, straight-chain or branched halogenoalkyl having 1 to 4carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,represents cycloalkyl having 3 to 6 carbon atoms which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine, bromine, methyl andethyl, represents phenyl, benzyl or phenethyl, it being possible foreach of the three last-mentioned radicals to be mono- to trisubstitutedby identical or different substituents selected from the groupconsisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms or phenoxy which is optionally substituted by halogen and/or alkylhaving 1 to 4 carbon atoms.

R¹ furthermore preferably represents a radical of the formula ##STR20##R¹¹ preferably represents hydrogen, straight-chain or branched alkylhaving 1 to 12 carbon atoms or represents cycloalkyl having 3 to 7carbon atoms which is optionally mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen andalkyl having 1 to 4 carbon atoms,

X³ preferably represents fluorine, chlorine, bromine, methyl, ethyl,methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy,difluoromethoxy, trifluoromethylthio, phenyl or phenoxy,

q preferably represents the numbers 0, 1, 2 or 3, where X³ representsidentical or different radicals if q represents 2 or 3, and

Y¹ preferably represents an oxygen atom, a CH₂ group or a direct bond.

R¹ furthermore preferably represents a radical of the formula ##STR21##R¹² preferably represents straight-chain or branched alkyl having 1 to 4carbon atoms, fluoroalkyl having 1 to 4 carbon atoms and 1 to 5 fluorineatoms, cycloalkyl having 3 to 6 carbon atoms which is optionally mono-to tri substituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, bromine, methyl and ethyl,cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and1 to 3 carbon atoms in the alkyl moiety, phenyl which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine and bromine orrepresents benzyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine and bromine,

X⁴ preferably represents fluorine, chlorine, bromine, nitro, methyl,ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl which is optionally mono- or disubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine and methyl or represents phenoxy which is optionallymono- or disubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine, bromine and methyl,

r preferably represents the numbers 0, 1, 2 or 3, where X⁴ representsidentical or different radicals if r represents 2 or 3 and

Y² preferably represents an oxygen atom or represents a CH₂ group.

R¹ furthermore preferably represents a radical of the formula ##STR22##A preferably represents alkanediyl having 2 or 3 carbon atoms which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyland tert-butyl,

X⁵ preferably represents fluorine, chlorine, bromine, methyl, ethyl,methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy,trifluoromethylthio, difluoromethoxy, phenyl which is optionally mono-to trisubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine and methyl and/or representsphenoxy which is optionally mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine and methyl and

s preferably represents the numbers 0, 1, 2 or 3, where X⁵ representsidentical or different radicals if s represents 2 or 3.

R¹ furthermore preferably represents a radical of the formula ##STR23##R¹³ preferably represents straight-chain or branched alkyl having 1 to 6carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,fluoroalkoxyalkyl having 1 to 3 carbon atoms and 1 to 5 fluorine atomsin the fluoroalkoxy moiety and 1 to 3 carbon atoms in the alkyl moiety,cycloalkyl having 3 to 6 carbon atoms which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, methyl and ethyl,cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and1 to 3 carbon atoms in the alkyl moiety, phenyl which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine and bromine orrepresents phenylalkyl having 1 or 2 carbon atoms in the alkyl moietywhich is optionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorineand bromine,

X⁶ preferably represents fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which isoptionally mono- or disubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine andmethyl or represents phenoxy which is optionally mono- or disubstitutedby identical or different substituents selected from the groupconsisting of fluorine, chlorine, bromine and methyl and

t preferably represents the numbers 0, 1, 2 or 3, where X⁶ representsidentical or different radicals if t represents 2 or 3.

R¹ furthermore preferably represents a radical of the formula ##STR24##R¹⁴ preferably represents straight-chain or branched alkyl having 1 to 4carbon atoms, fluoroalkyl having 1 to 4 carbon atoms and 1 to 5 fluorineatoms, cycloalkyl having 3 to 6 carbon atoms which is optionally mono-to trisubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, bromine, methyl and ethyl,cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and1 to 3 carbon atoms in the alkyl moiety, phenyl which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine and bromine orrepresents benzyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine and bromine,

X⁷ preferably represents fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which isoptionally mono- or disubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine andmethyl or represents phenoxy which is optionally mono- or disubstitutedby identical or different substituents selected from the groupconsisting of fluorine, chlorine, bromine and methyl,

u preferably represents the numbers 0, 1, 2 or 3, where X⁷ representsidentical or different radicals if u represents 2 or 3, and

Y³ preferably represents an oxygen atom or represents a CH₂ group.

R¹ furthermore also preferably represents a radical of the formula##STR25## R¹⁵ preferably represents straight-chain or branched alkylhaving 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and1 to 5 halogen atoms, phenyl which is optionally mono- to trisubstitutedby identical or different substituents selected from the groupconsisting of halogen, alkyl having 1 to 4 carbon atoms, halogenoalkylhaving 1 or 2 carbon atoms with 1 to 5 halogen atoms, alkoxy having 1 to4 carbon atoms and halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5halogen atoms or represents phenylalkyl having 1 to 4 carbon atoms inthe alkyl moiety which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 or2 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbonatoms and halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 halogenatoms,

X⁸ preferably represents fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which isoptionally mono- or disubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine andmethyl or represents phenoxy which is optionally mono- or disubstitutedby identical or different substituents selected from the groupconsisting of fluorine, chlorine, bromine and methyl and

v preferably represents the numbers 0, 1, 2 or 3, where X⁸ representsidentical or different radicals if v represents 2 or 3.

R particularly preferably represents straight-chain or branched alkylhaving 1 to 6 carbon atoms, straight-chain or branched halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 fluorine, chlorine and/or bromineatoms, phenyl which is optionally mono- to trisubstituted by identicalor different substituents selected from the group consisting offluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyland tert-butyl, phenylalkyl having 1 or 2 carbon atoms in the alkylmoiety which is optionally mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl andtert-butyl, straight-chain or branched alkoxy having 1 to 10 carbonatoms, straight-chain or branched alkylamino having 1 to 12 carbon atomsor represents phenylamino which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl,n-butyl and tert-butyl,

R¹ particularly preferably represents a radical of the formula ##STR26##R² particularly preferably represents straight-chain or branched alkylhaving 1 to 4 carbon atoms, it being possible for these radicals to bemono- to tetrasubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,methoxy, ethoxy, propoxy, isopropoxy, alkoximino having 1 or 2 carbonatoms in the alkoxy moiety, cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl,

or

particularly preferably represents straight-chain or branched alkenylhaving 2 to 5 carbon atoms, it being possible for each of these radicalsto be mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,methoxy, ethoxy, propoxy, isopropoxy, cyclopropyl, cyclobutyl,cyclopentyl and cyclohexyl,

or

particularly preferably represents cycloalkyl having 3 to 6 carbonatoms, it being possible for each of these radicals to be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, cyano, methyl, ethyl,propyl, isopropyl and tert-butyl,

or

particularly preferably represents phenylalkyl having 1 to 4 carbonatoms in the straight-chain or branched alkyl moiety, it being possiblefor the phenyl moiety to be mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy,methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,chlordifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio,methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl,nitro and cyano,

or

particularly preferably represents phenylalkenyl having 2 to 4 carbonatoms in the alkenyl moiety, it being possible for the phenyl moiety tobe mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano,

or

particularly preferably represents phenoxyalkyl having 1 to 4 carbonatoms in the straight-chain or branched oxyalkyl moiety, it beingpossible for the phenyl moiety to be mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy,ethoxy, methylthio, trifluoromethyl, trifluoromethoxy,trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy,chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl,methoximinomethyl, 1-methoximinoethyl, nitro and cyano,

or

particularly preferably represents phenyl which may be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano,

or

particularly preferably represents pyrazolyl, imidazolyl,1,2,4-triazolyl, pyrrolyl, furanyl, thienyl, thiazolyl, oxazolyl,pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl,quinazolinyl, indolyl, benzothienyl, benzofuranyl, benzothiazolyl orbenzimidazolyl, it being possible for each of these radicals to be mono-to trisubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,chlorodifluoromethylthio, hydroxymethyl, hydroxyethyl, hydroxyalkinylhaving 4 to 6 carbon atoms, methoxycarbonyl, ethoxycarbonyl,methoximinomethyl, 1-methoximinoethyl, nitro and/or cyano, formyl,dimethoxymethyl, acetyl and propionyl, and

R³ particularly preferably represents straight-chain or branched alkylhaving 1 to 4 carbon atoms, it being possible for these radicals to bemono- to tetrasubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,methoxy, ethoxy, propoxy, isopropoxy, alkoximino having 1 or 2 carbonatoms in the alkoxy moiety, cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl,

or

particularly preferably represents straight-chain or branched alkenylhaving 2 to 5 carbon atoms, it being possible for each of these radicalsto be mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,methoxy, ethoxy, propoxy, isopropoxy, cyclopropyl, cyclobutyl,cyclopentyl and cyclohexyl,

or

particularly preferably represents cycloalkyl having 3 to 6 carbonatoms, it being possible for each of these radicals to be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, cyano, methyl, ethyl,propyl, isopropyl and tert-butyl,

or

particularly preferably represents phenylalkyl having 1 to 4 carbonatoms in the straight-chain or branched alkyl moiety, it being possiblefor the phenyl moiety to be mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy,methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio,methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl,nitro and cyano,

or

particularly preferably represents phenylalkenyl having 2 to 4 carbonatoms in the alkenyl moiety, it being possible for the phenyl moiety tobe mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano,

or

particularly preferably represents phenoxyalkyl having 1 to 4 carbonatoms in the straight-chain or branched oxyalkyl moiety, it beingpossible for the phenyl moiety to be mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy,ethoxy, methylthio, trifluoromethyl, trifluoromethoxy,trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy,chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl,methoximinomethyl, 1-methoximinoethyl, nitro and cyano,

or

particularly preferably represents phenyl which may be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano,

or

particularly preferably represents pyrazolyl, imidazolyl,1,2,4-triazolyl, pyrrolyl, furanyl, thienyl, thiazolyl, oxazolyl,pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl,quinazolinyl, indolyl, benzothienyl, benzofuranyl, benzothiazolyl orbenzimidazolyl, it being possible for each of these radicals to be mono-to trisubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,chlorodifluoromethylthio, hydroxymethyl, hydroxyethyl, hydroxyalkinylhaving 4 to 6 carbon atoms, methoxycarbonyl, ethoxycarbonyl,methoximinomethyl, 1-methoximinoethyl, nitro and/or cyano, formyl,dimethoxymethyl, acetyl and propionyl.

R¹ furthermore particularly preferably represents a radical of theformula ##STR27## R⁴ particularly preferably represents methyl, ethyl,n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl,fluoro-tert-butyl, difluoro-tert-butyl, cycloalkyl having 3 to 6 carbonatoms which is optionally mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine and bromine, represents naphthyl or represents phenyl which maybe mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,nitro, phenyl, phenoxy, methyl, ethyl, tert-butyl, methoxy, ethoxy,trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl,trifluoromethoxy, difluoromethoxy and trifluoromethylthio, and

R⁵ particularly preferably represents phenyl which may be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, methyl, ethyl,isobutyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl,difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxyand trifluoromethylthio.

R¹ furthermore particularly preferably represents a radical of theformula ##STR28## R⁶ particularly preferably represents hydrogen,methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl,tert-butyl or n-pentyl,

R⁷ particularly preferably represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

X¹ particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl,tert-butyl, methoxy, ethoxy, phenyl, phenoxy, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy ortrifluoromethylthio and

m also particularly preferably represents the numbers 0, 1 or 2,

it being possible for X¹ to represent identical or different radicals ifm represents 2.

R¹ particularly preferably represents a radical of the formula ##STR29##R⁸ particularly preferably represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

R⁹ particularly preferably represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

X² particularly preferably represents fluorine, chlorine, bromine,cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, methoxy, ethoxy, trifluoromethyl,trichloromethyl, difluoromethyl, trichloromethoxy, trifluoromethoxy,difluoromethoxy, difluorochloromethoxy or phenyl,

n also particularly preferably represents the numbers 0 or 1 and

p also particularly preferably represents the numbers 0, 1 or 2,

it being possible for X² to represent identical or different radicals ifp represents 2.

R¹ furthermore particularly preferably represents a radical of theformula ##STR30## R¹⁰ particularly preferably represents methyl, ethyl,n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl,halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorineand/or bromine atoms, cyclopropyl, cyclopentyl or cyclohexyl, each ofwhich is optionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, methyl and ethyl, and also represents phenyl, benzyl orphenethyl, it being possible for each of the three last-mentionedradicals to be mono- to trisubstituted in the phenyl moiety by identicalor different substituents selected from the group consisting offluorine, chlorine, bromine, methyl, ethyl, methoxy, methylthio,trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy,trifluoromethylthio, phenyl and phenoxy.

R¹ furthermore particularly preferably represents a radical of theformula ##STR31## R¹¹ particularly preferably represents hydrogen,straight-chain or branched alkyl having 1 to 6 carbon atoms orrepresents cyclopropyl, cyclopentyl or cyclohexyl, each of which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, methyl and ethyl,

X³ particularly preferably represents fluorine, chlorine, bromine,methyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl orphenoxy,

q also particularly preferably represents the numbers 0, 1, 2 or 3, itbeing possible for X³ to represent identical or different radicals if qrepresents 2 or 3 and

Y¹ also particularly preferably represents an oxygen atom, a CH₂ groupor a direct bond.

R¹ furthermore particularly preferably represents a radical of theformula ##STR32## R¹² particularly preferably represents methyl,isopropyl, tert-butyl, fluoro-tert-butyl, difluoro-tert-butyl,represents cyclopropyl, cyclopentyl or cyclohexyl, each of which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorineand methyl, represents cycloalkylalkyl having 3 to 6 carbon atoms in thecycloalkyl moiety and 1 or 2 carbon atoms in the alkyl moiety,represents phenyl which is optionally mono- or disubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine and bromine or represents benzyl which isoptionally mono- or disubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine and bromine,

X⁴ particularly preferably represents fluorine, chlorine, bromine,nitro, methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy,

r also particularly preferably represents the numbers 0, 1, 2 or 3, itbeing possible for X⁴ to represent identical or different radicals if rrepresents 2 or 3 and

Y² also particularly preferably represents an oxygen atom or representsa CH₂ group.

R¹ furthermore particularly preferably represents a radical of theformula ##STR33## A particularly preferably represents alkanediyl having2 or 3 carbon atoms which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl,n-butyl, i-butyl, sec-butyl and tert-butyl,

X⁵ particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, difluoromethoxy, phenyl which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorineand methyl and/or represents phenoxy which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine and methyl and

s also particularly preferably represents the numbers 0, 1, 2 or 3, itbeing possible for X⁵ to represent identical or different radicals if srepresents 2 or 3.

R¹ furthermore particularly preferably represents a radical of theformula ##STR34## R¹³ particularly preferably represents methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl,halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 fluorine, chlorineand/or bromine atoms, fluoroalkoxyalkyl having 1 or 2 carbon atoms and 1to 5 fluorine atoms in the fluoroalkoxy moiety and 1 or 2 carbon atomsin the alkyl moiety, cyclopropyl, cyclopentyl or cyclohexyl, each ofwhich is optionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorineand methyl, represents cycloalkylalkyl having 3 to 6 carbon atoms in thecycloalkyl moiety and 1 or 2 carbon atoms in the alkyl moiety, phenylwhich is optionally mono- or disubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorineand bromine or represents benzyl which is optionally mono- ordisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine and bromine,

X⁶ particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy and

t also particularly preferably represents the numbers 0, 1, 2 or 3, itbeing possible for X⁶ to represent identical or different radicals if trepresents 2 or 3.

R¹ furthermore particularly preferably represents a radical of theformula ##STR35## R¹⁴ particularly preferably represents methyl,isopropyl, tert-butyl, fluoro-tert-butyl, difluoro-tert-butyl,cyclopropyl, cyclopentyl or cyclohexyl, each of which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine and methyl, representscycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and1 or 2 carbon atoms in the alkyl moiety, phenyl which is optionallymono- or disubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine and bromine orrepresents benzyl which is optionally mono- or disubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine and bromine,

X⁷ particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy,

Y³ also particularly preferably represents an oxygen atom or representsa CH₂ group, and

u also particularly preferably represents the numbers 0, 1, 2 or 3,where X⁷ represents identical or different radicals if u represents 2 or3.

R¹ moreover also preferably represents a radical of the formula##STR36## R¹⁵ particularly preferably represents methyl, ethyl,n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl,fluoro-tert-butyl, difluoro-tert-butyl, phenyl which is optionally mono-or disubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, methyl, ethyl,trifluoromethyl, trichloromethyl, methoxy, ethoxy, trifluoromethoxy anddifluoromethoxy or represents phenylalkyl having 1 or 2 carbon atoms inthe alkyl moiety which is optionally mono- or disubstituted in thephenyl moiety by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, methyl, ethyl,trifluoromethyl, trichloromethyl, methoxy, ethoxy, trifluoromethoxy anddifluoromethoxy,

X⁸ particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy, and

v also particularly preferably represents the numbers 0, 1, 2 or 3, itbeing possible for X⁸ to represent identical or different radicals if vrepresents 2 or 3.

Preferred compounds according to the invention are also additionproducts of acids and those acyl-mercapto-triazolyl derivatives of theformula (I) in which R and R¹ have those meanings which have beenmentioned as being particularly preferred for these substituents.

The acids which can be added preferably include hydrohalic acids, suchas, for example, hydrochloric acid and hydrobromic acid, in particularhydrochloric acid, furthermore phosphoric acid, nitric acid, mono- andbifunctional carboxylic acids and hydrocarboxylic acids, such as, forexample, acetic acid, maleic acid, succinic acid, fumaric acid, tartaricacid, citric acid, salicylic acid, sorbic acid and lactic acid, and alsosulphonic acids, such as, for example, p-toluenesulphonic acid and1,5-naphthalenedisulphonic acid, and also saccharin and thiosaccharin.

Preferred compounds according to the invention are moreover additionproducts of salts of metals of main groups II to IV and sub-groups I andII and also IV to VIII of the Periodic Table of the Elements and thoseacyl-mercapto-triazolyl derivatives of the formula (I) in which R and R¹have those meanings which have been mentioned as being preferred forthese substituents.

Particular preference is given here to salts of copper, zinc, manganese,magnesium, tin, iron and nickel. Suitable anions of these salts arethose which are derived from those acids which lead to physiologicallyacceptable addition products. Acids of this kind which are particularlypreferred in this context are hydrohalic acids, such as, for example,hydrochloric acid and hydrobromic acid, furthermore phosphoric acid,nitric acid and sulphuric acid.

The mercapto-triazoles required as starting materials in the preparationof the substances according to the invention can be present in the"mercapto" form of the formula ##STR37## or in the tautomeric "thiono"form of the formula ##STR38##

It can therefore not be excluded that some or all of the substancesaccording to the invention are derived from the "thiono" form of theformula (IIa). This means that the substances according to the inventionare either present as substances of the formula ##STR39##

("mercapto" form)

or of the formula ##STR40##

("thiono" form)

or as mixtures of substances of the formulae (I) and (Ia). Forsimplicity, only the structure of the "mercapto" form is given in eachcase.

Examples of substances according to the invention include theacyl-mercapto-triazolyl derivatives listed in the tables below.

                                      TABLE 1                                     __________________________________________________________________________                                         (Ib)                                                                            #STR41##                                  -                                                                          R.sup.2           R.sup.3  R                                                  __________________________________________________________________________                                 #STR42##                                                                    --C(CH.sub.3).sub.3 --CH.sub.3                        -                                                                                                       --C(CH.sub.3).sub.3 --C.sub.2 H.sub.5                                         -                                                                             --C(CH.sub.3).sub.3                                                           #STR45##                                            -                                                                                                       --C(CH.sub.3).sub.3 --O--CH.sub.3                   -                                                                                                       --C(CH.sub.3).sub.3                                                           #STR48##                                            -                                                                                                       --C(CH.sub.3).sub.3 --NH--CH.sub.3                  -                                                                                                       --C(CH.sub.3).sub.3                                                           #STR51##                                            -                                                                                                       --C(CH.sub.3).sub.3 --CH.sub.3                      -                                                                                                       --C(CH.sub.3).sub.3 --C.sub.2 H.sub.5                                         -                                                                             --C(CH.sub.3).sub.3                                                           #STR55##                                            -                                                                                                       --C(CH.sub.3).sub.3 --OCH.sub.3                     -                                                                                                       --C(CH.sub.3).sub.3                                                           #STR58##                                            -                                                                                                       --C(CH.sub.3).sub.3 --NH--CH.sub.3                  -                                                                                                       --C(CH.sub.3).sub.3 --CH.sub.3                      -                                                                                                       --C(CH.sub.3).sub.3 --C.sub.2 H.sub.5                                         -                                                                             --C(CH.sub.3).sub.3                                                           #STR63##                                            -                                                                                                       --C(CH.sub.3).sub.3 --NH--CH.sub.3                  -                                                                                                       #STR65##                                                                      --CH.sub.3                                          -                                                                                                       #STR67##                                                                      --C.sub.2 H.sub.5                                   -                                                                                                       #STR69##                                                                      #STR70##                                                                      #STR71##                                            -                                                                                                       #STR72##                                                                      --NH--CH.sub.3                                      -                                                                                                       --C.sub.4 H.sub.9 -n --CH.sub.3                     -                                                                                                       --C.sub.4 H.sub.9 -n --C.sub.2 H.sub.5                                        -                                                                             --C.sub.4 H.sub.9 -n                                                          #STR77##                                            -                                                                                                       --C.sub.4 H.sub.9 -n --NH--CH.sub.3                 -                                                                                                       #STR79##                                                                      --CH.sub.3                                          -                                                                                                       #STR81##                                                                      --OCH.sub.3                                         -                                                                                                       #STR83##                                                                      #STR84##                                                                      #STR85##                                            -                                                                                                       #STR86##                                                                      --NH--CH.sub.3                                      -                                                                                                       --C(CH.sub.3).sub.3 --CH.sub.3                      -                                                                                                       --C(CH.sub.3).sub.3 --C.sub.2 H.sub.5                                         -                                                                             --C(CH.sub.3).sub.3                                                           #STR91##                                            -                                                                                                       --C(CH.sub.3).sub.3 --OCH.sub.3                     - Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 -- --C(CH.sub.3).sub.3 --CH.sub.3                                  Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 -- --C(CH.su                               b.3).sub.3 --C.sub.2 H.sub.5                          - Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 --                                                                  --CH.sub.3                                          - Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 --                                                                  --C.sub.2 H.sub.5                                   - Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 --                                                                  --CH.sub.3                                          - Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 --                                                                  --OCH.sub.3                                         -                                                                                                       --C(CH.sub.3).sub.3 --CH.sub.3                      -                                                                                                       --C(CH.sub.3).sub.3 --C.sub.2 H.sub.5                                         -                                                                             #STR99##                                                                      --CH.sub.3                                          -                                                                                                       #STR101##                                                                     --C.sub.2 H.sub.5                                   -                                                                                                       #STR103##                                                                     --C.sub.2 H.sub.5                                   -                                                                                                       #STR105##                                                                     --C.sub.2 H.sub.5                                   -                                                                                                       #STR107##                                                                     --CH.sub.3                                          - Cl.sub.2 CH--CCl.sub.2 --                                                                             --CH.sub.3                                          -                                                                                                       --C(CH.sub.3).sub.3 --CH.sub.3                      -                                                                                                       --C(CH.sub.3).sub.3 --CH.sub.3                      -                                                                                                       --C(CH.sub.3).sub.3                                                          ##STR113##                                        __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________                                       (Ic)                                                                            #STR114##                                R.sup.4              R.sup.5     R                                            __________________________________________________________________________                                       #STR115##                                                                     #STR116##                                                                   --CH.sub.3                                      -                                                                                                             #STR117##                                                                     --CH.sub.3                                    -                                                                                                             #STR119##                                                                     --CH.sub.3                                    -                                                                                                             #STR121##                                                                     --CH.sub.3                                    -                                                                                                             #STR123##                                                                     --CH.sub.3                                    -                                                                                                             #STR125##                                                                     --CH.sub.3                                    -                                                                                                             #STR127##                                                                     --CH.sub.3                                    -                                                                                                             #STR129##                                                                     --CH.sub.3                                    -                                                                                                             #STR131##                                                                     --CH.sub.3                                    -                                                                                                             #STR133##                                                                     --CH.sub.3                                    -                                                                                                             #STR135##                                                                     --CH.sub.3                                    -                                                                                                             #STR137##                                                                     --CH.sub.3                                    -                                                                                                             #STR139##                                                                     --CH.sub.3                                    -                                                                                                             #STR141##                                                                     --CH.sub.3                                    -                                                                                                             #STR143##                                                                     --CH.sub.3                                    -                                                                                                             #STR145##                                                                     --CH.sub.3                                    -                                                                                                             #STR147##                                                                     --CH.sub.3                                    -                                                                                                             #STR149##                                                                     --CH.sub.3                                    -                                                                                                             #STR151##                                                                     --CH.sub.3                                    -                                                                                                             #STR153##                                                                     --CH.sub.3                                    -                                                                                                             #STR155##                                                                     --CH.sub.3                                    -                                                                                                             #STR157##                                                                     --CH.sub.3                                    -                                                                                                             #STR159##                                                                     --CH.sub.3                                    -                                                                                                             #STR161##                                                                     --CH.sub.3                                    -                                                                                                             #STR163##                                                                     --CH.sub.3                                    -                                                                                                             #STR165##                                                                     --CH.sub.3                                    -                                                                                                             #STR167##                                                                     --CH.sub.3                                    -                                                                                                             #STR169##                                                                     --CH.sub.3                                    -                                                                                                             #STR171##                                                                     --CH.sub.3                                    -                                                                                                             #STR173##                                                                     --CH.sub.3                                    -                                                                                                             #STR175##                                                                     --CH.sub.3                                    -                                                                                                             #STR177##                                                                     --CH.sub.3                                    -                                                                                                             #STR179##                                                                     --CH.sub.3                                    -                                                                                                             #STR181##                                                                     --CH.sub.3                                    -                                                                                                             #STR183##                                                                     --CH.sub.3                                    -                                                                                                             #STR185##                                                                     --CH.sub.3                                    -                                                                                                             #STR187##                                                                     --CH.sub.3                                    -                                                                                                             #STR189##                                                                     --CH.sub.3                                    -                                                                                                             #STR191##                                                                     --CH.sub.3                                    -                                                                                                             #STR193##                                                                     --CH.sub.3                                    -                                                                                                             #STR195##                                                                     --CH.sub.3                                    -                                                                                                             #STR197##                                                                     --CH.sub.3                                    -                                                                                                             #STR199##                                                                     --CH.sub.3                                    -                                                                                                             #STR201##                                                                     --CH.sub.3                                    -                                                                                                             #STR203##                                                                     --CH.sub.3                                    -                                                                                                             #STR205##                                                                     --CH.sub.3                                    -                                                                                                             #STR207##                                                                     --CH.sub.3                                    -                                                                                                             #STR209##                                                                     --CH.sub.3                                    - --CH.sub.3                                                                                                  --CH.sub.3                                    - --CH.sub.3                                                                                                  --CH.sub.3                                    - --CH.sub.3                                                                                                  --CH.sub.3                                    - --C(CH.sub.3).sub.3                                                                                         --CH.sub.3                                    -                                                                                                             #STR215##                                                                     --CH.sub.3                                    -                                                                                                             #STR217##                                                                     --OCH.sub.3                                   -                                                                                                             #STR219##                                                                     --OCH.sub.3                                   -                                                                                                             #STR221##                                                                     --OCH.sub.3                                   -                                                                                                             #STR223##                                                                     --OCH.sub.3                                   -                                                                                                             #STR225##                                                                     --OCH.sub.3                                   -                                                                                                             #STR227##                                                                     --OCH.sub.3                                   -                                                                                                             #STR229##                                                                     --OCH.sub.3                                   -                                                                                                             #STR231##                                                                     --OCH.sub.3                                   -                                                                                                             #STR233##                                                                     --OCH.sub.3                                   -                                                                                                             #STR235##                                                                     --OCH.sub.3                                   -                                                                                                             #STR237##                                                                     --OCH.sub.3                                   -                                                                                                             #STR239##                                                                     --OCH.sub.3                                   -                                                                                                             #STR241##                                                                     --OCH.sub.3                                   -                                                                                                             #STR243##                                                                     --OCH.sub.3                                   -                                                                                                             #STR245##                                                                     --OCH.sub.3                                   -                                                                                                             #STR247##                                                                     --OCH.sub.3                                   -                                                                                                             #STR249##                                                                     --OCH.sub.3                                   -                                                                                                             #STR251##                                                                     --OCH.sub.3                                   -                                                                                                             #STR253##                                                                     --OCH.sub.3                                   -                                                                                                             #STR255##                                                                     --OCH.sub.3                                   -                                                                                                             #STR257##                                                                     --OCH.sub.3                                   -                                                                                                             #STR259##                                                                     --OCH.sub.3                                   -                                                                                                             #STR261##                                                                     --OCH.sub.3                                   -                                                                                                             #STR263##                                                                     --OCH.sub.3                                   -                                                                                                             #STR265##                                                                     --OCH.sub.3                                   -                                                                                                             #STR267##                                                                     --OCH.sub.3                                   -                                                                                                             #STR269##                                                                     --OCH.sub.3                                   -                                                                                                             #STR271##                                                                     --OCH.sub.3                                   -                                                                                                             #STR273##                                                                     --OCH.sub.3                                   -                                                                                                             #STR275##                                                                     --OCH.sub.3                                   -                                                                                                             #STR277##                                                                     --OCH.sub.3                                   -                                                                                                             #STR279##                                                                     --OCH.sub.3                                   -                                                                                                             #STR281##                                                                     --OCH.sub.3                                   -                                                                                                             #STR283##                                                                     --OCH.sub.3                                   -                                                                                                             #STR285##                                                                     --OCH.sub.3                                   -                                                                                                             #STR287##                                                                     --OCH.sub.3                                   -                                                                                                             #STR289##                                                                     --OCH.sub.3                                   -                                                                                                             #STR291##                                                                     --OCH.sub.3                                   -                                                                                                             #STR293##                                                                     --OCH.sub.3                                   -                                                                                                             #STR295##                                                                     --OCH.sub.3                                   -                                                                                                             #STR297##                                                                     --OCH.sub.3                                   -                                                                                                             #STR299##                                                                     --OCH.sub.3                                   -                                                                                                             #STR301##                                                                     --OCH.sub.3                                   -                                                                                                             #STR303##                                                                     --OCH.sub.3                                   -                                                                                                             #STR305##                                                                     --OCH.sub.3                                   -                                                                                                             #STR307##                                                                     --OCH.sub.3                                   -                                                                                                             #STR309##                                                                     --OCH.sub.3                                   -                                                                                                             #STR311##                                                                     --OCH.sub.3                                   -                                                                                                             #STR313##                                                                     --OCH.sub.3                                   - --CH.sub.3                                                                                                  --OCH.sub.3                                   - --CH.sub.3                                                                                                  --OCH.sub.3                                   - --CH.sub.3                                                                                                  --OCH.sub.3                                   - --C(CH.sub.3).sub.3                                                                                         --OCH.sub.3                                   -                                                                                                             #STR319##                                                                     --OCH.sub.3                                __________________________________________________________________________

                  TABLE 3                                                         ______________________________________                                                                      (Id)                                                                            #STR321##                                        -                                                                          R.sup.6    R.sup.7  R          X.sup.1.sub.m                                  ______________________________________                                        --CH.sub.3 --CH.sub.3                                                                             --CH.sub.3 4-Br                                             --CH.sub.3 --CH.sub.3 --CH.sub.3 4-F                                          --CH.sub.3 --CH.sub.3 --CH.sub.3 2,4-Cl.sub.2                                 --CH.sub.3 H --CH.sub.3 4-Cl                                                  --CH.sub.3 --CH.sub.3 --CH.sub.3 --                                           --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CH.sub.3                                   --CH.sub.3 --CH.sub.3 --CH.sub.3 2-F, 4-Cl                                    --C.sub.2 H.sub.5 H --CH.sub.3 4-Cl                                           --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl                           --C.sub.3 H.sub.7 -n H --CH.sub.3 4-Cl                                        --C.sub.2 H.sub.5 H --CH.sub.3 2,4-Cl.sub.2                                   --C.sub.2 H.sub.5 H --CH.sub.3 4-F                                            --C.sub.2 H.sub.5 H --CH.sub.3 4-Br                                            - --C.sub.2 H.sub.5 H --CH.sub.3                                                                            #STR322##                                       - --C.sub.2 H.sub.5 H --CH.sub.3 4-C.sub.4 H.sub.9 -t                        --C.sub.3 H.sub.7 -i H --CH.sub.3 4-Cl                                        --C.sub.5 H.sub.11 -n H --CH.sub.3 4-Cl                                        - --CH.sub.3 --CH.sub.3 --CH.sub.3                                                                          #STR323##                                       - --CH.sub.3 --CH.sub.3 --CH.sub.3 4-C.sub.4 H.sub.9 -t                      --C.sub.4 H.sub.9 -n H --CH.sub.3 4-Cl                                        --C.sub.4 H.sub.9 -i H --CH.sub.3 4-Cl                                        --CH.sub.3 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl                                  --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-Cl                                        --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-Br                                        --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-F                                         --CH.sub.3 --CH.sub.3 --OCH.sub.3 2,4-Cl.sub.2                                --CH.sub.3 H --OCH.sub.3 4-Cl                                                 --CH.sub.3 --CH.sub.3 --OCH.sub.3 --                                          --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-CH.sub.3                                  --CH.sub.3 --CH.sub.3 --OCH.sub.3 2-F, 4-Cl                                   --C.sub.2 H.sub.5 H --OCH.sub.3 4-Cl                                          --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 --OCH.sub.3 4-Cl                          --C.sub.3 H.sub.7 -n H --OCH.sub.3 4-Cl                                       --C.sub.2 H.sub.5 H --OCH.sub.3 2,4-Cl.sub.2                                  --C.sub.2 H.sub.5 H --OCH.sub.3 4-F                                           --C.sub.2 H.sub.5 H --OCH.sub.3 4-Br                                           - --C.sub.2 H.sub.5 H --OCH.sub.3                                                                           #STR324##                                       - --C.sub.2 H.sub.5 H --OCH.sub.3 4-C.sub.4 H.sub.9 -t                       --C.sub.3 H.sub.7 -i H --OCH.sub.3 4-Cl                                       --C.sub.5 H.sub.11 -n H --OCH.sub.3 4-Cl                                       - --CH.sub.3 --CH.sub.3 --OCH.sub.3                                                                         #STR325##                                       - --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-C.sub.4 H.sub.9 -t                     --C.sub.4 H.sub.9 -n H --OCH.sub.3 4-Cl                                       --C.sub.4 H.sub.9 -i H --OCH.sub.3 4-Cl                                       --CH.sub.3 --C.sub.2 H.sub.5 --OCH.sub.3 4-Cl                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 2-Cl                                         --CH.sub.3 --CH.sub.3 --CH.sub.3 2,3-Cl.sub.2                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CF.sub.3                                   --CH.sub.3 --CH.sub.3 --CH.sub.3 4-OCF.sub.3                                  --CH.sub.3 --CH.sub.3 --CH.sub.3 4-Cl                                       ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                                                      (Ie)                                                                            #STR326##                                        -                                                                          R.sup.8   R.sup.9   R         X.sup.2.sub.p                                                                          n                                      ______________________________________                                        --CH.sub.3                                                                              --CH.sub.3                                                                              --CH.sub.3                                                                              4-Br     0                                        --CH.sub.3 --CH.sub.3 --CH.sub.3 4-F 0                                        --CH.sub.3 --CH.sub.3 --CH.sub.3 2,4-Cl.sub.2 0                               --CH.sub.3 H --CH.sub.3 4-Cl 0                                                --CH.sub.3 --CH.sub.3 --CH.sub.3 -- 0                                         --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CH.sub.3 0                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 2-F, 4-Cl 0                                  --C.sub.2 H.sub.5 H --CH.sub.3 4-Cl 0                                         --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl 0                         --C.sub.3 H.sub.7 -n H --CH.sub.3 4-Cl 0                                      --C.sub.2 H.sub.5 H --CH.sub.3 2,4-Cl.sub.2 0                                 --C.sub.2 H.sub.5 H --CH.sub.3 4-F 0                                          --C.sub.2 H.sub.5 H --CH.sub.3 4-Br 0                                         --C.sub.2 H.sub.5 H --CH.sub.3 4-NO.sub.2 0                                   --C.sub.2 H.sub.5 H --CH.sub.3 4-C.sub.4 H.sub.9 -t 0                         --C.sub.3 H.sub.7 -i H --CH.sub.3 4-Cl 0                                      --C.sub.5 H.sub.11 -n H --CH.sub.3 4-Cl 0                                     --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CN 0                                       --CH.sub.3 --CH.sub.3 --CH.sub.3 4-C.sub.4 H.sub.9 -t 0                       --C.sub.4 H.sub.9 -n H --CH.sub.3 4-Cl 0                                      --C.sub.4 H.sub.9 -i H --CH.sub.3 4-Cl 0                                      --CH.sub.3 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl 0                                --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-Cl 0                                      --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-Br 0                                      --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-F 0                                       --CH.sub.3 --CH.sub.3 --OCH.sub.3 2,4-Cl.sub.2 0                              --CH.sub.3 H --OCH.sub.3 4-Cl 0                                               --CH.sub.3 --CH.sub.3 --OCH.sub.3 -- 0                                        --CH.sub.3 --CH.sub.3 --OCH.sub.3 4--CH.sub.3 0                               --CH.sub.3 --CH.sub.3 --OCH.sub.3 2-F, 4-Cl 0                                 --C.sub.2 H.sub.5 H --OCH.sub.3 4-Cl 0                                        --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 --OCH.sub.3 4-Cl 0                        --C.sub.3 H.sub.7 -n H --OCH.sub.3 4-Cl 0                                     --C.sub.2 H.sub.5 H --OCH.sub.3 2,4-Cl.sub.2 0                                --C.sub.2 H.sub.5 H --OCH.sub.3 4-F 0                                         --C.sub.2 H.sub.5 H --OCH.sub.3 4-Br 0                                        --C.sub.2 H.sub.5 H --OCH.sub.3 4-NO.sub.2 0                                  --C.sub.2 H.sub.5 H --OCH.sub.3 4-C.sub.4 H.sub.9 -t 0                        --C.sub.3 H.sub.7 -i H --OCH.sub.3 4-Cl 0                                     --C.sub.5 H.sub.11 -n H --OCH.sub.3 4-Cl 0                                    --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-CN 0                                      --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-C.sub.4 H.sub.9 -t 0                      --C.sub.4 H.sub.9 -n H --OCH.sub.3 4-Cl 0                                     --C.sub.4 H.sub.9 -i H --OCH.sub.3 4-Cl 0                                     --CH.sub.3 --C.sub.2 H.sub.5 --OCH.sub.3 4-Cl 0                               --CH.sub.3 --CH.sub.3 --CH.sub.3 4-OCH.sub.3 0                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCH.sub.3 0                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-CF.sub.3 0                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CF.sub.3 0                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCF.sub.3 0                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCHF.sub.2 0                               --CH.sub.3 --CH.sub.3 --CH.sub.3 4-OCF.sub.3 0                                --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-OCH.sub.3 0                               --CH.sub.3 --CH.sub.3 --OCH.sub.3 2-OCH.sub.3 0                               --CH.sub.3 --CH.sub.3 --OCH.sub.3 2-CF.sub.3 0                                --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-CF.sub.3 0                                --CH.sub.3 --CH.sub.3 --OCH.sub.3 2-OCF.sub.3 0                               --CH.sub.3 --CH.sub.3 --OCH.sub.3 2-OCHF.sub.2 0                              --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-OCF.sub.3 0                               --CH.sub.3 --CH.sub.3 --CH.sub.3 4-Br 1                                       --CH.sub.3 --CH.sub.3 --CH.sub.3 4-F 1                                        --CH.sub.3 --CH.sub.3 --CH.sub.3 2,4-Cl.sub.2 1                               --CH.sub.3 H --CH.sub.3 4-Cl 1                                                --CH.sub.3 --CH.sub.3 --CH.sub.3 -- 1                                         --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CH.sub.3 1                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 2-F, 4-Cl 1                                  --C.sub.2 H.sub.5 H --CH.sub.3 4-Cl 1                                         --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl 1                         --C.sub.3 H.sub.7 -n H --CH.sub.3 4-Cl 1                                      --C.sub.2 H.sub.5 H --CH.sub.3 2,4-Cl.sub.2 1                                 --C.sub.2 H.sub.5 H --CH.sub.3 4-F 1                                          --C.sub.2 H.sub.5 H --CH.sub.3 4-Br 1                                         --C.sub.2 H.sub.5 H --CH.sub.3 4-NO.sub.2 1                                   --C.sub.2 H.sub.5 H --CH.sub.3 4-C.sub.4 H.sub.9 -t 1                         --C.sub.3 H.sub.7 -i H --CH.sub.3 4-Cl 1                                      --C.sub.5 H.sub.11 -n H --CH.sub.3 4-Cl 1                                     --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CN 1                                       --CH.sub.3 --CH.sub.3 --CH.sub.3 4-C.sub.4 H.sub.9 -t 1                       --C.sub.4 H.sub.9 -n H --CH.sub.3 4-Cl 1                                      --CH.sub.3 --CH.sub.3 --CH.sub.3 4-Cl 1                                       --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-Cl 1                                      --C.sub.4 H.sub.9 -i H --CH.sub.3 4-Cl 1                                      --CH.sub.3 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl 1                                --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-Cl 1                                      --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-Br 1                                      --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-F 1                                       --CH.sub.3 --CH.sub.3 --OCH.sub.3 2,4-Cl.sub.2 1                              --CH.sub.3 H --OCH.sub.3 4-Cl 1                                               --CH.sub.3 --CH.sub.3 --OCH.sub.3 -- 1                                        --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-CH.sub.3 1                                --CH.sub.3 --CH.sub.3 --OCH.sub.3 2-F, 4-Cl 1                                 --C.sub.2 H.sub.5 H --OCH.sub.3 4-Cl 1                                        --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 --OCH.sub.3 4-Cl 1                        --C.sub.3 H.sub.7 -n H --OCH.sub.3 4-Cl 1                                     --C.sub.2 H.sub.5 H --OCH.sub.3 2,4-Cl.sub.2 1                                --C.sub.2 H.sub.5 H --OCH.sub.3 4-F 1                                         --C.sub.2 H.sub.5 H --OCH.sub.3 4-Br 1                                        --C.sub.2 H.sub.5 H --OCH.sub.3 4-NO.sub.2 1                                  --C.sub.2 H.sub.5 H --OCH.sub.3 4-C.sub.4 H.sub.9 -t 1                        --C.sub.3 H.sub.7 -i H --OCH.sub.3 4-Cl 1                                     --C.sub.5 H.sub.11 -n H --OCH.sub.3 4-Cl 1                                    --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-CN 1                                      --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-C.sub.4 H.sub.9 -t 1                      --C.sub.4 H.sub.9 -n H --OCH.sub.3 4-Cl 1                                     --C.sub.4 H.sub.9 -i H --OCH.sub.3 4-Cl 1                                     --CH.sub.3 --C.sub.2 H.sub.5 --OCH.sub.3 4-Cl 1                               --CH.sub.3 --CH.sub.3 --CH.sub.3 4-OCH.sub.3 1                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCH.sub.3 1                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-CF.sub.3 1                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CF.sub.3 1                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCF.sub.3 1                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCHF.sub.2 1                               --CH.sub.3 --CH.sub.3 --CH.sub.3 4-OCF.sub.3 1                                --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-OCH.sub.3 1                               --CH.sub.3 --CH.sub.3 --OCH.sub.3 2-OCH.sub.3 1                               --CH.sub.3 --CH.sub.3 --OCH.sub.3 2-CF.sub.3 1                                --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-CF.sub.3 1                                --CH.sub.3 --CH.sub.3 --OCH.sub.3 2-OCF.sub.3 1                               --CH.sub.3 --CH.sub.3 --OCH.sub.3 2-OCHF.sub.2 1                              --CH.sub.3 --CH.sub.3 --OCH.sub.3 4-OCF.sub.3 1                               --CH.sub.3 --CH.sub.3 --CH.sub.3 2-Cl 0                                       --CH.sub.3 --CH.sub.3 --CH.sub.3 2,3-Cl.sub.2 0                               --CH.sub.3 --CH.sub.3 --CH.sub.3 2-Cl 1                                       --CH.sub.3 --CH.sub.3 --CH.sub.3 4-Cl 0                                     ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                                                     (If)                                                                            #STR327##                                         -                                                                          R.sup.10                 R                                                    ______________________________________                                                                   #STR328##                                                                   --CH.sub.3                                              -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            - --C.sub.4 H.sub.9 -n --CH.sub.3                                            --C(CH.sub.3).sub.3 --CH.sub.3                                                --CH(CH.sub.3).sub.2 --CH.sub.3                                                -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            - --CH.sub.2 --CH(CH.sub.3).sub.2 --CH.sub.3                                  -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --CH.sub.3                                            -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           - --C.sub.4 H.sub.9 -n --OCH.sub.3                                           --C(CH.sub.3).sub.3 --OCH.sub.3                                               --CH(CH.sub.3).sub.2 --OCH.sub.3                                               -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           - --CH.sub.2 --CH(CH.sub.3).sub.2 --OCH.sub.3                                 -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --OCH.sub.3                                           -                                                                                                     --CH.sub.3                                            -                                                                                                     --OCH.sub.3                                           -                                                                                                     --NH--CH.sub.3                                     ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                                                      (Ig)                                                                            #STR403##                                        -                                                                          X.sup.3.sub.q Y.sup.1 R.sup.11     R                                          ______________________________________                                          4-Cl CH.sub.2 H --CH.sub.3                                                    4-CF.sub.3 CH.sub.2 H --CH.sub.3                                              4-OCF.sub.3 CH.sub.2 H --CH.sub.3                                             2,4-Cl.sub.2 CH.sub.2 H --CH.sub.3                                            4-CH.sub.3 CH.sub.2 H --CH.sub.3                                              2-Cl CH.sub.2 H --CH.sub.3                                                    2-F CH.sub.2 H --CH.sub.3                                                     4-F CH.sub.2 H --CH.sub.3                                                     2-OCHF.sub.2 CH.sub.2 H --CH.sub.3                                            4-Cl O H --CH.sub.3                                                           4-CF.sub.3 O H --CH.sub.3                                                     4-OCF.sub.3 O H --CH.sub.3                                                    2,4-Cl.sub.2 O H --CH.sub.3                                                   4-CH.sub.3 O H --CH.sub.3                                                     2-Cl O H --CH.sub.3                                                           2-F O H --CH.sub.3                                                            4-F O H --CH.sub.3                                                            2-OCHF.sub.2 O H --CH.sub.3                                                   4-Cl -- H --CH.sub.3                                                          4-CF.sub.3 -- H --CH.sub.3                                                    4-OCF.sub.3 -- H --CH.sub.3                                                   2,4-Cl.sub.2 -- H --CH.sub.3                                                  4-CH.sub.3 -- H --CH.sub.3                                                    2-Cl -- H --CH.sub.3                                                          2-F -- H --CH.sub.3                                                           4-F -- H --CH.sub.3                                                           2-OCHF.sub.2 -- H --CH.sub.3                                                  4-Cl CH.sub.2 --CH.sub.3 --CH.sub.3                                           4-CF.sub.3 CH.sub.2 --CH.sub.3 --CH.sub.3                                     4-OCF.sub.3 CH.sub.2 --CH.sub.3 --CH.sub.3                                    2,4-Cl.sub.2 CH.sub.2 --CH.sub.3 --CH.sub.3                                   4-CH.sub.3 CH.sub.2 --CH.sub.3 --CH.sub.3                                     2-Cl CH.sub.2 --CH.sub.3 --CH.sub.3                                           2-F CH.sub.2 --CH.sub.3 --CH.sub.3                                            4-F CH.sub.2 --CH.sub.3 --CH.sub.3                                            2-OCHF.sub.2 CH.sub.2 --CH.sub.3 --CH.sub.3                                   4-Cl O --CH.sub.3 --CH.sub.3                                                  4-CF.sub.3 O --CH.sub.3 --CH.sub.3                                            2,4-Cl.sub.2 O --CH.sub.3 --CH.sub.3                                          4-OCF.sub.3 O --CH.sub.3 --CH.sub.3                                           2-F O --CH.sub.3 --CH.sub.3                                                   2-OCHF.sub.2 O --CH.sub.3 --CH.sub.3                                          4-Cl -- --CH.sub.3 --CH.sub.3                                                 4-CF.sub.3 -- --CH.sub.3 --CH.sub.3                                           2,4-Cl.sub.2 -- --CH.sub.3 --CH.sub.3                                         4-OCF.sub.3 -- --CH.sub.3 --CH.sub.3                                          2-F -- --CH.sub.3 --CH.sub.3                                                  2-OCHF.sub.2 -- --CH.sub.3 --CH.sub.3                                         4-Cl CH.sub.2 C.sub.4 H.sub.9 -n --CH.sub.3                                   2,4-Cl.sub.2 CH.sub.2 --CH(CH.sub.3).sub.2 --CH.sub.3                         4-OCF.sub.3 CH.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3                            - 4-Cl CH.sub.2                                                                                                 --CH.sub.3                                  - 4-Cl CH.sub.2                                                                                                 --CH.sub.3                                  - 4-Cl CH.sub.2                                                                                                 --CH.sub.3                                  - 4-Cl CH.sub.2                                                                                                 --CH.sub.3                                  - 2,4,6-Cl.sub.3 CH.sub.2 --CH.sub.3 --CH.sub.3                               -                                                                                                               CH.sub.2 --CH.sub.3 --CH.sub.3                                                -                                                                             CH.sub.2 --CH.sub.3 --CH.sub.3                                                - 4-Cl CH.sub.2 H --OCH.sub.3                                                4-CF.sub.3 CH.sub.2 H --OCH.sub.3                                             4-OCF.sub.3 CH.sub.2 H --OCH.sub.3                                            2,4-Cl.sub.2 CH.sub.2 H --OCH.sub.3                                           4-CH.sub.3 CH.sub.2 H --OCH.sub.3                                             2-Cl CH.sub.2 H --OCH.sub.3                 2-F CH.sub.2 H --OCH.sub.3                                                    4-F CH.sub.2 H --OCH.sub.3                                                    2-OCHF.sub.2 CH.sub.2 H --OCH.sub.3                                           4-Cl O H --OCH.sub.3                                                          4-CF.sub.3 O H --OCH.sub.3                                                    4-OCF.sub.3 O H --OCH.sub.3                                                   2,4-Cl.sub.2 O H --OCH.sub.3                                                  4-CH.sub.3 O H --OCH.sub.3                                                    2-Cl O H --OCH.sub.3                                                          2-F O H --OCH.sub.3                                                           4-F O H --OCH.sub.3                                                           2-OCHF.sub.2 O H --OCH.sub.3                                                  4-Cl -- H --OCH.sub.3                                                         4-CF.sub.3 -- H --OCH.sub.3                                                   4-OCF.sub.3 -- H --OCH.sub.3                                                  2,4-Cl.sub.2 -- H --OCH.sub.3                                                 4-CH.sub.3 -- H --OCH.sub.3                                                   2-Cl -- H --OCH.sub.3                                                         2-F -- H --OCH.sub.3                                                          4-F -- H --OCH.sub.3                                                          2-OCHF.sub.2 -- H --OCH.sub.3                                                 4-Cl CH.sub.2 --CH.sub.3 --OCH.sub.3                                          4-CF.sub.3 CH.sub.2 --CH.sub.3 --OCH.sub.3                                    4-OCF.sub.3 CH.sub.2 --CH.sub.3 --OCH.sub.3                                   2,4-Cl.sub.2 CH.sub.2 --CH.sub.3 --OCH.sub.3                                  4-CH.sub.3 CH.sub.2 --CH.sub.3 --OCH.sub.3                                    2-Cl CH.sub.2 --CH.sub.3 --OCH.sub.3                                          2-F CH.sub.2 --CH.sub.3 --OCH.sub.3                                           4-F CH.sub.2 --CH.sub.3 --OCH.sub.3                                           2-OCHF.sub.2 CH.sub.2 --CH.sub.3 --OCH.sub.3                                  4-Cl O --CH.sub.3 --OCH.sub.3                                                 4-CF.sub.3 O --CH.sub.3 --OCH                                                 2,4-Cl.sub.2 O --CH.sub.3 --OCH.sub.3                                         4-OCF.sub.3 O --CH.sub.3 --OCH.sub.3                                          2-F O --CH.sub.3 --OCH.sub.3                                                  2-OCHF.sub.2 O --CH.sub.3 --OCH.sub.3                                         4-Cl -- --CH.sub.3 --OCH.sub.3                                                4-CF.sub.3 -- --CH.sub.3 --OCH.sub.3                                          2,4-Cl.sub.2 -- --CH.sub.3 --OCH.sub.3                                        4-OCF.sub.3 -- --CH.sub.3 --OCH.sub.3                                         2-F -- --CH.sub.3 --OCH.sub.3                                                 2-OCHF.sub.2 -- --CH.sub.3 --OCH.sub.3                                        4-Cl CH.sub.2 --C.sub.4 H.sub.9 -n --OCH.sub.3                                2,4-Cl.sub.2 CH.sub.2 --CH(CH.sub.3).sub.2 --OCH.sub.3                        4-OCF.sub.3 CH.sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3                           - 4-Cl CH.sub.2                                                                                                 --OCH.sub.3                                 - 4-Cl CH.sub.2                                                                                                 --OCH.sub.3                                 - 4-Cl CH.sub.2                                                                                                 --OCH.sub.3                                 - 4-Cl CH.sub.2                                                                                                 --OCH.sub.3                                 - 2,4,6-Cl.sub.3 CH.sub.2 --CH.sub.3 --OCH.sub.3                              -                                                                                                               CH.sub.2 --CH.sub.3 --OCH.sub.3                                               -                                                                             --CH.sub.2 --CH.sub.3 --OCH.sub.3                                             - 4-OCF.sub.3 CH.sub.2 --CH.sub.3                                           --OCH.sub.3                                ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                                                      (Ih)                                                                            #STR416##                                        -                                                                          X.sup.4.sub.r                                                                            R.sup.12       R          Y.sup.2                                  ______________________________________                                          2,4-Cl.sub.2                                                                                                       --CH.sub.3 O                              - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-Br --C(CH.sub.3).sub.3 --CH.sub.3 O                                      -- --C(CH.sub.3).sub.3 --CH.sub.3 O                                           4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                          2-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                         3-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                         4-F --C(CH.sub.3).sub.3 --CH.sub.3 O                                           -                                                                                                                 --C(CH.sub.3).sub.3 --CH.sub.3 O                                              -                                                                             --C(CH.sub.3).sub.3 --CH.sub.3 O                                              - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3                                          --CH.sub.3 O                               2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                             3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 O                         2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                               4-Cl --CH.sub.3 --CH.sub.3 O                                                   - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-CF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                4-OCF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                  2-OCHF.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 O                                 4-OCH.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                   - 2,4-Cl.sub.2                                                                                                    --OCH.sub.3 O                             - 4-Cl                                                                                                            --OCH.sub.3 O                             - 4-Br --C(CH.sub.3).sub.3 --OCH.sub.3 O                                     -- --C(CH.sub.3).sub.3 --OCH.sub.3 O                                          4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 O                         2-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 O                                        3-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 O                                        4-F --C(CH.sub.3).sub.3 --OCH.sub.3 O                                          -                                                                                                                 --C(CH.sub.3).sub.3 --OCH.sub.3 O                                             -                                                                             --C(CH.sub.3).sub.3 --OCH.sub.3 O                                             - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3                                          --OCH.sub.3 O                              2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 O                            3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3 O                        2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 O                              4-Cl --CH.sub.3 --OCH.sub.3 O                                                  - 4-Cl                                                                                                            --OCH.sub.3 O                             - 4-CF.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 O                               4-OCF.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 O                                 2-OCHF.sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3 O                                4-OCH.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 O                                  - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-Cl                                                                                                            --OCH.sub.3 O                             - 4-Cl                                                                                                            --OCH.sub.3 O                             - 2,4-Cl.sub.2                                                                                                    --CH.sub.3 CH.sub.2                       - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-Br --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                               -- --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                    4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                   2-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                  3-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                  4-F --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                    -                                                                                                                 --C(CH.sub.3).sub.3 --CH.sub.3                                              CH.sub.2                                    -                                                                                                                 --C(CH.sub.3).sub.3 --CH.sub.3                                              CH.sub.2                                    - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                       2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                      3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                  2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                        4-Cl --CH.sub.3 --CH.sub.3 CH.sub.2                                            - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-CF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                         4-OCF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                           2-OCHF.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                          4-OCH.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                            - 2,4-Cl.sub.2                                                                                                    --OCH.sub.3 CH.sub.2                      - 4-Cl                                                                                                            --OCH.sub.3 CH.sub.2                      - 4-Br --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                              -- --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                                   4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                  2-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                                 3-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                                 4-F --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                                   -                                                                                                                 --C(CH.sub.3).sub.3 --OCH.sub.3                                             CH.sub.2                                    -                                                                                                                 --C(CH.sub.3).sub.3 --OCH.sub.3                                             CH.sub.2                                    - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                      2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                     3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                 2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                       4-Cl --CH.sub.3 --OCH.sub.3 CH.sub.2                                           - 4-Cl                                                                                                            --OCH.sub.3 CH.sub.2                      - 4-CF.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                        4-OCF.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                          2-OCHF.sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                         4-OCH.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                           - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-Cl                                                                                                            --OCH.sub.3 CH.sub.2                      - 4-Cl                                                                                                            --OCH.sub.3 CH.sub.2                      - 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                      4-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 O                                        4-Cl --C(CH.sub.3).sub.3 --NH--CH.sub.3 O                                   ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                                                     (Ii)                                                                            #STR445##                                         -                                                                          X.sup.5.sub.s                                                                            A                  R                                               ______________________________________                                        2,4-Cl.sub.2                                                                             --(CH.sub.2).sub.3 --                                                                            --CH.sub.3                                        2,4-Cl.sub.2 --(CH.sub.2).sub.2 -- --CH.sub.3                                  - 4-Cl                                                                                                     --CH.sub.3                                       - 4-CF.sub.3                                                                                               --CH.sub.3                                       -                                                                                                          --CH.sub.2 --CH.sub.2 -- --CH.sub.3                                           -                                                                             #STR449##                                                                     --CH.sub.3                                       - 4-F                                                                                                      --CH.sub.3                                       - 4-OCF.sub.3                                                                                              --CH.sub.3                                       - 2,4-F.sub.2                                                                                              --CH.sub.3                                       - 2-OCHF.sub.2                                                                                             --CH.sub.3                                       -                                                                                                          --CH.sub.2).sub.3 -- --CH.sub.3                  - 2,4,6-Cl.sub.3                                                                                           --CH.sub.3                                       - --                                                                                                       --CH.sub.3                                       - 2,4-F.sub.2                                                                                              --CH.sub.3                                       -                                                                                                          #STR459##                                                                     --CH.sub.3                                       - 2,4-Cl.sub.2                                                                                             --CH.sub.3                                       -                                                                                                          #STR462##                                                                     --CH.sub.3                                       - 2,4-Cl.sub.2                                                                                             --CH.sub.3                                       -                                                                                                          #STR465##                                                                     --CH.sub.3                                       - 2,4-Cl.sub.2                                                                                             --CH.sub.3                                       - 2,4-Cl.sub.2 --(CH.sub.2).sub.3 -- --OCH.sub.3                             2,4-Cl.sub.2 --(CH.sub.2).sub.2 -- --OCH.sub.3                                 - 4-Cl                                                                                                     --OCH.sub.3                                      - 4-CF.sub.3                                                                                               --OCH.sub.3                                      -                                                                                                          --CH.sub.2 --CH.sub.2 -- --OCH.sub.3                                          -                                                                             #STR471##                                                                     --OCH.sub.3                                      - 4-F                                                                                                      --OCH.sub.3                                      - 4-OCF.sub.3                                                                                              --OCH.sub.3                                      - 2,4-F.sub.2                                                                                              --OCH.sub.3                                      - 2-OCHF.sub.2                                                                                             --OCH.sub.3                                      -                                                                                                          --(CH.sub.2).sub.3 -- --OCH.sub.3                                             - 2,4,6-Cl.sub.3                                                              --OCH.sub.3                                      - --                                                                                                       --OCH.sub.3                                      - 2,4-F.sub.2                                                                                              --OCH.sub.3                                      -                                                                                                          #STR481##                                                                     --OCH.sub.3                                      - 2,4-Cl.sub.2                                                                                             --OCH.sub.3                                      -                                                                                                          #STR484##                                                                     --OCH.sub.3                                      - 2,4-Cl.sub.2                                                                                             --OCH.sub.3                                      -                                                                                                          #STR487##                                                                     --OCH.sub.3                                      - 2,4-Cl.sub.2                                                                                             --OCH.sub.3                                      - 2,4-Cl.sub.2                                                                                             --CH.sub.3                                       - 2,4-Cl.sub.2                                                                                             --OCH.sub.3                                      - 2,4-Cl.sub.2                                                                                             --NH--CH.sub.3                                ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                                                      (Ik)                                                                            #STR493##                                        -                                                                          X.sup.6.sub.t                                                                           R.sup.13           R                                                ______________________________________                                        2,4-Cl.sub.2                                                                            --CH.sub.3         --CH.sub.3                                         2,4-Cl.sub.2 --C.sub.2 H.sub.5 --CH.sub.3                                     2,4-Cl.sub.2 --CH(CH.sub.3).sub.2 --CH.sub.3                                  4-Cl --C.sub.3 H.sub.7 -n --CH.sub.3                                          2,4-Cl.sub.2 --C.sub.4 H.sub.9 -n --CH.sub.3                                   - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3                                2-Cl --C.sub.3 H.sub.7 -n --CH.sub.3                                          2-OCF.sub.3 --C.sub.3 H.sub.7 -n --CH.sub.3                                   4-CF.sub.3 --C.sub.3 H.sub.7 -n --CH.sub.3                                    4--CH.sub.3 --C.sub.3 H.sub.7 -n --CH.sub.3                                   2,4,6-Cl.sub.3 --C.sub.3 H.sub.7 -n --CH.sub.3                                 - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 4-F --C.sub.3 H.sub.7 -n --CH.sub.3                                         - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 2,4-Cl.sub.2                                                                                            --CH.sub.3                                        - 2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --CH.sub.3                                           2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.2                                        --CH.sub.3 --CH.sub.3                              4-Cl --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --CH.sub.3                          2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.3 --CH.sub.3                              4-F --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --CH.sub.3                           2-Cl --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --CH.sub.3                          2,4-Cl.sub.2 --CH.sub.3 --OCH.sub.3                                           2,4-Cl.sub.2 --C.sub.2 H.sub.5 --OCH.sub.3                                    2,4-Cl.sub.2 --CH(CH.sub.3).sub.2 --OCH.sub.3                                 4-Cl --C.sub.3 H.sub.7 -n --OCH.sub.3                                         2,4-Cl.sub.2 --C.sub.4 H.sub.9 -n --OCH.sub.3                                  - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3                               2-Cl --C.sub.3 H.sub.7 -n --OCH.sub.3                                         2-OCF.sub.3 --C.sub.3 H.sub.7 -n --OCH.sub.3                                  4-CF.sub.3 --C.sub.3 H.sub.7 -n --OCH.sub.3                                   4-CH.sub.3 --C.sub.3 H.sub.7 -n --OCH.sub.3                                   2,4,6-Cl.sub.3 --C.sub.3 H.sub.7 -n --OCH.sub.3                                - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 4-F --C.sub.3 H.sub.7 -n --OCH.sub.3                                        - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 2,4-Cl.sub.2                                                                                            --OCH.sub.3                                       - 2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --OCH.sub.3                                          2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.2                                        --CH.sub.3 --OCH.sub.3                             4-Cl --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --OCH.sub.3                         2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.3 --OCH.sub.3                             4-F --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --OCH.sub.3                          2-Cl --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --OCH.sub.3                         2,4-Cl.sub.2 --CH.sub.2 --CF.sub.3 --CH.sub.3                                 2,4-Cl.sub.2 --CF.sub.2 --CF.sub.3 --CH.sub.3                                 2,4-Cl.sub.2 --C.sub.3 H.sub.7 -n --CH.sub.3                                  2,4-Cl.sub.2 --C.sub.3 H.sub.7 -n --OCH.sub.3                                 2,4-Cl.sub.2 --C.sub.3 H.sub.7 -n --NH--CH.sub.3                            ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                                                      (Im)                                                                            #STR518##                                        -                                                                          X.sup.7.sub.u                                                                            R.sup.14       R          Y.sup.3                                  ______________________________________                                          2,4-Cl.sub.2                                                                                                       --CH.sub.3 O                              - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-Br --C(CH.sub.3).sub.3 --CH.sub.3 O                                      -- --C(CH.sub.3).sub.3 --CH.sub.3 O                                           4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                          2-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                         3-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                         4-F --C(CH.sub.3).sub.3 --CH.sub.3 O                                           -                                                                                                                 --C(CH.sub.3).sub.3 --CH.sub.3 O                                              -                                                                             --C(CH.sub.3).sub.3 --CH.sub.3 O                                              - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3                                          --CH.sub.3 O                               2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                             3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 O                         2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                               4-Cl --CH.sub.3 --CH.sub.3 O                                                   - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-CF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                4-OCF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                  2-OCHF.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 O                                 4-OCH.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                   - 2,4-Cl.sub.3                                                                                                    --OCH.sub.3 O                             - 4-Cl                                                                                                            --OCH.sub.3 O                             - 4-Br --C(CH.sub.3).sub.3 --OCH.sub.3 O                                     -- --C(CH.sub.3).sub.3 --OCH.sub.3 O                                          4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 O                         2-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 O                                        3-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 O                                        4-F --C(CH.sub.3).sub.3 --OCH.sub.3 O                                          -                                                                                                                 --C(CH.sub.3).sub.3 --OCH.sub.3 O                                             -                                                                             --C(CH.sub.3).sub.3 --OCH.sub.3 O                                             - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3                                          --OCH.sub.3 O                              2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 O                            3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3 O                        2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 O                              4-Cl --CH.sub.3 --OCH.sub.3 O                                                  - 4-Cl                                                                                                            --OCH.sub.3 O                             - 4-CF.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 O                               4-OCF.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 O                                 2-OCHF.sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3 O                                4-OCH.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 O                                  - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-Cl                                                                                                            --OCH.sub.3 O                             - 4-Cl                                                                                                            --OCH.sub.3 O                             - 2,4-Cl.sub.2                                                                                                    --CH.sub.3 CH.sub.2                       - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-Br --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                               -- --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                    4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                   2-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                  3-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                  4-F --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                    -                                                                                                                 --C(CH.sub.3).sub.3 --CH.sub.3                                              CH.sub.2                                    -                                                                                                                 --C(CH.sub.3).sub.3 --CH.sub.3                                              CH.sub.2                                    - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                       2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                      3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                  2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                        4-Cl --CH.sub.3 --CH.sub.3 CH.sub.2                                            - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-CF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                         4-OCF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                           2-OCHF.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                          4-OCH.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                            - 2,4-Cl.sub.2                                                                                                    --OCH.sub.3 CH.sub.2                      - 4-Cl                                                                                                            --OCH.sub.3 CH.sub.2                      - 4-Br --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                              -- --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                                   4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                  2-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                                 3-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                                 4-F --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                                   -                                                                                                                 --C(CH.sub.3).sub.3 --OCH.sub.3                                             CH.sub.2                                    -                                                                                                                 --C(CH.sub.3).sub.3 --OCH.sub.3                                             CH.sub.2                                    - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                      2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                     3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                 2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                       4-Cl --CH.sub.3 --OCH.sub.3 CH.sub.2                                           - 4-Cl                                                                                                            --OCH.sub.3 CH.sub.2                      - 4-CF.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                        4-OCF.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                          2-OCHF.sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                         4-OCH.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3 CH.sub.2                           - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-Cl                                                                                                            --OCH.sub.3 CH.sub.2                      - 4-Cl                                                                                                            --OCH.sub.3 CH.sub.2                      - 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                      4-Cl --C(CH.sub.3).sub.3 --OCH.sub.3 O                                        4-Cl --C(CH.sub.3).sub.3 --NH--CH.sub.3 O                                   ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                                                      (In)                                                                            #STR547##                                        -                                                                          X.sup.8.sub.v                                                                            R.sup.15            R                                              ______________________________________                                        Cl         --C.sub.4 H.sub.9 -n                                                                              --CH.sub.3                                       2-Cl --C.sub.4 H.sub.9 -n --CH.sub.3                                          2,4-Cl.sub.2 --C.sub.4 H.sub.9 -n --CH.sub.3                                  4-Br --C.sub.4 H.sub.9 -n --CH.sub.3                                          4-F --C.sub.4 H.sub.9 -n --CH.sub.3                                           4-C(CH.sub.3).sub.3 --C.sub.4 H.sub.9 -n --CH.sub.3                            -                                                                                                           --C.sub.4 H.sub.9 -n --CH.sub.3                 - 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3                                        2-Cl --C(CH.sub.3).sub.3 --CH.sub.3                                           2,4-Cl.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3                                   2,4,6-Cl.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3                                 4-CF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3                                     2-OCHF.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3                                    - 4-Cl                                                                                                      --CH.sub.3                                      - 4-Cl                                                                                                      --CH.sub.3                                      - 4-Cl                                                                                                      --CH.sub.3                                      - 4-Cl                                                                                                      --CH.sub.3                                      - 4-Cl                                                                                                      --CH.sub.3                                      - 4-Cl                                                                                                      --CH.sub.3                                      - --                                                                                                        --CH.sub.3                                      - 4-Cl --C.sub.4 H.sub.9 -n --OCH.sub.3                                      2-Cl --C.sub.4 H.sub.9 -n --OCH.sub.3                                         2,4-Cl.sub.2 --C.sub.4 H.sub.9 -n --OCH.sub.3                                 4-Br --C.sub.4 H.sub.9 -n --OCH.sub.3                                         4-F --C.sub.4 H.sub.9 -n --OCH.sub.3                                          4-C(CH.sub.3).sub.3 --C.sub.4 H.sub.9 -n --OCH.sub.3                           -                                                                                                           --C.sub.4 H.sub.9 -n --OCH.sub.3                                              - 4-Cl --C(CH.sub.3).sub.3 --OCH.sub.3                                       2-Cl --C(CH.sub.3).sub.3 --OCH.sub.3                                          2,4-Cl.sub.2 --C(CH.sub.3).sub.3 --OCH.sub                                   .3                                               2,4,6-Cl.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3                                4-CF.sub.3 --C(CH.sub.3).sub.3 --OCH.sub.3                                    2-OCHF.sub.2 --C(CH.sub.3).sub.3 --OCH.sub.3                                   - 4-Cl                                                                                                      --OCH.sub.3                                     - 4-Cl                                                                                                      --OCH.sub.3                                     - 4-Cl                                                                                                      --OCH.sub.3                                     - 4-Cl                                                                                                      --OCH.sub.3                                     - 4-Cl                                                                                                      --OCH.sub.3                                     - 4-Cl                                                                                                      --OCH.sub.3                                     - --                                                                                                        --OCH.sub.3                                     - --                                                                                                        --OCH.sub.3                                     - --                                                                                                        --CH.sub.3                                      - --                                                                                                        --NH--CH.sub.3                               ______________________________________                                    

Using2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-olas starting material and acetyl chloride as reaction component, thecourse of the process according to the invention (variant a) can beillustrated by the equation below. ##STR567##

Using2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-olas starting material and methyl chloroformate as reaction component, thecourse of the process according to the invention (variant b) can beillustrated by the equation below. ##STR568##

Using2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-olas starting material and methyl isocyanate as reaction component, thecourse of the process according to the invention (variant c) can beillustrated by the equation below. ##STR569##

The formula (II) provides a general definition of the mercapto-triazolesrequired as starting materials for carrying out the process according tothe invention. In this formula, R¹ preferably has those meanings whichhave already been mentioned in connection with the description of thesubstances of the formula (I) according to the invention as beingpreferred for this radical.

The mercapto-triazoles of the formula (II) have hitherto not beendisclosed- They can be prepared by reacting triazoles of the formula##STR570## in which R¹ is as defined above

either

α) successively with strong bases and sulphur in the presence of adiluent, followed by hydrolysis with water, if appropriate in thepresence of an acid,

or

β) with sulphur in the presence of a high-boiling diluent, followed, ifappropriate, by treatment with water and, if appropriate, with acid.

The formula (VI) provides a general definition of the triazoles requiredas starting materials for carrying out the process for preparingmercapto-triazoles of the formula (II). In this formula, R¹ preferablyhas those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred for this radical.

The triazoles of the formula (VI) are known or can be prepared by knownmethods (cf. EP-A 0 015 756, EP-A 0 040 345, EP-A 0 052 424, EP-A 0 061835, EP-A 0 297 345, EP-A 0 094 564, EP-A 0 196 038, EP-A 0 267 778,EP-A 0 378 953, EP-A 0 044 605, EP-A 0 069 442, EP-A 0 055 833, EP-A 0301 393, DE-A 2 324 010, DE-A 2 737 489, DE-A 2 551 560, EP-A 0 065 485,DE-A 2 735 872. EP-A 0 234 242, DE-A 2 201 063, EP-A 0 145 294 and DE-A3 721 786).

Suitable bases for carrying out the above process (α) for preparingmercaptotriazoles of the formula (II) are all strong alkali metal baseswhich are customary for such reactions. Preference is given to usingn-butyl-lithium, lithium diisopropyl-amide, sodium hydride, sodium amideand also potassium tert-butoxide in a mixture withtetramethylethylene-diamine (=TMEDA).

Suitable diluents for carrying out the above process (α) for preparingmercaptotriazoles of the formula (II) are all inert organic solventswhich are customary for such reactions. Preference is given to usingethers, such as tetrahydrofuran, dioxane, diethyl ether and1,2-dimethoxyethane, furthermore liquid ammonia or else strongly polarsolvents, such as dimethyl sulphoxide.

Both when carrying out the above process (α) and also the process (β),sulphur is preferably employed in the form of a powder.

When carrying out the above process (α), water, if appropriate in thepresence of an acid, is employed for hydrolysis. Suitable acids here areall inorganic or organic acids which are customary for such reactions.Preference is given to using acetic acid, dilute sulphuric acid anddilute hydrochloric acid. However, it is also possible to carry out thehydrolysis using aqueous ammonium chloride solution.

When carrying out the above process (α), the reaction temperatures canbe varied within a certain range. In general, the process is carried outat temperatures between -70° C. and +20° C., preferably between -70° C.and 0° C.

The above processes (α) and (β) are generally carried out underatmospheric pressure. However, it is also possible to operate underelevated or reduced pressure. Thus, in particular when carrying out theprocess (β), operation under elevated pressure is possible.

When carrying out the above process (α), generally 2 to 3 equivalents,preferably 2.0 to 2.5 equivalents, of strong base and subsequently anequivalent amount or else an excess of sulphur are employed per mole oftriazole of the formula (VI). The reaction can be carried out under anatmosphere of protective gas, for example under nitrogen or argon.Work-up is carried out by customary methods. In general, the reactionmixture is extracted with an organic solvent which is only sparinglysoluble in water, the combined organic phases are dried and concentratedand the residue that remains is, if appropriate, purified byrecrystallization and/or chromatography.

Suitable diluents for carrying out the above process (β) are allhigh-boiling organic solvents which are customary for such reactions.Preference is given to using amides, such as dimethylformamide anddimethylacetamide, furthermore heterocyclic compounds, such asN-methyl-pyrrolidone, and also ethers, such as diphenyl ether.

When carrying out the above process (β), a treatment with water and, ifappropriate, with acid, can be carried out, if appropriate, after thereaction. This treatment is carried out like the hydrolysis in thepractice of the process (α).

When carrying out the above process (β), the reaction temperatures canalso be varied within a relatively large range. In general, the reactionis carried out at temperatures between 150° C. and 300° C., preferablybetween 180° C. and 250° C.

When carrying out the above process (β), generally 1 to 5 mol,preferably 1.5 to 3 mol, of sulphur are employed per mole of triazole ofthe formula (VI). Work-up is carried out by customary methods. Ingeneral, the reaction mixture is extracted with an organic solvent whichis only sparingly soluble in water, the combined organic phases aredried and concentrated and the residue that remains is, if appropriate,freed of any impurities that may be present using customary methods,such as recrystallization or chromatography.

The formula (III) provides a general definition of the acyl halidesrequired as reaction components for carrying out variant (a) of theprocess according to the invention. In this formula, R¹⁶ preferablyrepresents straight-chain or branched alkyl having 1 to 8 carbon atoms,straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and1 to 5 identical or different halogen atoms, phenyl which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of halogen and alkyl having 1 to 4 carbonatoms or represents phenylalkyl having 1 to 4 carbon atoms in the alkylmoiety which is optionally mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen andalkyl having 1 to 4 carbon atoms. Hal also preferably representschlorine or bromine.

R¹⁶ particularly preferably represents straight-chain or branched alkylhaving 1 to 6 carbon atoms, straight-chain or branched halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 fluorine, chlorine and/or bromineatoms, phenyl which is optionally mono- to trisubstituted by identicalor different substituents selected from the group consisting offluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyland tert-butyl or represents phenylalkyl having 1 or 2 carbon atoms inthe alkyl moiety which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl,n-butyl and tert-butyl, Hal particularly preferably represents chlorine.

The acyl halides of the formula (III) are known or can be prepared byknown methods.

Suitable acid binders for carrying out variant (a) of the processaccording to the invention are all customary inorganic or organic bases.Preference is given to using alkali metal hydrides, such as lithiumhydride or sodium hydride, furthermore alkaline earth metal hydroxidesor alkali metal hydroxides such as sodium hydroxide, calcium hydroxide,potassium hydroxide, or else ammonium hydroxide, alkali metalcarbonates, such as sodium carbonate, potassium carbonate, potassiumbicarbonate, sodium bicarbonate, alkali metal acetates or alkaline earthmetal acetates such as sodium acetate, potassium acetate, calciumacetate, and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline, pyridine,N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

Suitable diluents for carrying out variant (a) of the process accordingto the invention are all customary inert organic solvents. Preference isgiven to using aromatic hydrocarbons, such as toluene, xylene ordecalin, furthermore halogenated hydrocarbons, such as dichloromethane,chloroform, carbon tetrachloride, dichloroethane or trichloroethane,moreover ethers, such as diethyl ether, diisopropyl ether, methyltert-butyl ether, methyl tert-amyl ether, dioxane or tetrahydrofuran,and furthermore nitriles, such as acetonitrile, propionitrile, n- orisobutyronitrile.

When carrying out variant (a) of the process according to the invention,the reaction temperatures can be varied within a relatively wide range.In general, the process is carried out at temperatures between -20° C.and +120° C., preferably at temperatures between 0° C. and +100° C.

Both variant (a) and variants (b) or (c) of the process according to theinvention are generally carried out under atmospheric pressure. However,it is also possible to operate under elevated or reduced pressure.

When carrying out variant (a) of the process according to the invention,generally 1 to 3 mol of acyl halide of the formula (III) and anequivalent amount or else an excess of acid binder are employed per moleof mercapto-triazole of the formula (II). Work-up is carried out bycustomary methods. In general, the reaction mixture is, if appropriateafter prior addition of a little alcohol, concentrated under reducedpressure, the residue that remains is extracted with an organic solventwhich is only sparingly miscible with water and the combined organicphases are concentrated under reduced pressure. The product that isobtained can, if appropriate, be freed of any impurities that may stillbe present using customary methods, for example recrystallization orchromatography.

The formula (IV) provides a general definition of the halogenoformatesrequired as reaction components for carrying out variant (b) of theprocess according to the invention. In this formula, R¹⁷ preferablyrepresents straight-chain or branched alkyl having 1 to 12 carbon atoms.Hal¹ also preferably represents chlorine or bromine.

R¹⁷ particularly preferably represents straight-chain or branched alkylhaving 1 to 10 carbon atoms. Hal¹ particularly preferably representschlorine.

The halogenoformates of the formula (IV) are known or can be prepared byknown methods.

Suitable acid binders for carrying out variant (b) of the processaccording to the invention are all inorganic or organic bases which arecustomary for such reactions. Preference is given to using those acidbinders which have already been mentioned in connection with thedescription of process variant (a) as being preferred.

Suitable diluents for carrying out variant (b) of the process accordingto the invention are again all inert organic solvents which arecustomary for such reactions. Preference is given to using thosesolvents which have already been mentioned in connection with thedescription of process variant (a) as being preferred.

When carrying out variant (b) of the process according to the invention,the reaction temperatures can again be varied within a certain range. Ingeneral, the reaction is carried out at temperatures between -20° C. and+100° C., preferably between -10° C. and +80° C.

When carrying out variant (b) of the process according to the invention,generally 1 to 2 mol of halogenoformate of the formula (IV) and anequivalent amount or else an excess of acid binder are employed per moleof mercapto-triazole of the formula (II). Work-up is carried out bycustomary methods. In general, the reaction mixture is diluted with anorganic solvent which is only sparingly miscible with water and thenextracted with weakly basic aqueous solution, and the organic phase isthen dried and concentrated under reduced pressure. The product that isobtained can, if appropriate, be freed of any impurities that may stillbe present using customary methods, for example recrystallization orchromatography.

The formula (V) provides a general definition of the isocyanatesrequired as reaction components for carrying out variant (c) of theprocess according to the invention. In this formula, R¹⁸ preferablyrepresents straight-chain or branched alkyl having 1 to 14 carbon atomsor represents phenyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen and alkyl having 1 to 4 carbon atoms.

R¹⁸ particularly preferably represents straight-chain or branched alkylhaving 1 to 12 carbon atoms or represents phenyl which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine, bromine, methyl, ethyl,n-propyl, isopropyl, n-butyl and tert-butyl.

The isocyanates of the formula (V) are known or can be prepared by knownmethods.

Suitable catalysts for carrying out variant (c) of the process accordingto the invention are all reaction promoters which are customary for suchreactions. Preference is given to using amines, such as triethylamine,pyridine, dimethylaminopyridine and diazabicyclo-undecene (DBU).

Suitable diluents for carrying out variant (c) of the process accordingto the invention are again all inert organic solvents which arecustomary for such reactions. Preference is given to using thosesolvents which have already been mentioned in connection with thedescription of process variant (a) as being preferred.

When carrying out variant (c) of the process according to the invention,the reaction temperatures can again be varied within a certain range. Ingeneral, the reaction is carried out at temperatures between -20° C. and+100° C., preferably between 0° C. and +80° C.

When carrying out variant (c) of the process according to the invention,generally 1 to 1.5 mol of isocyanate of the formula (V) and a smallamount of catalyst are employed per mole of mercapto-triazole of theformula (II). Work-up is carried out by customary methods. In general,the reaction mixture is concentrated under reduced pressure and theproduct that remains is freed of any impurities that may still bepresent using customary methods, for example recrystallization orchromatography.

The acyl-mercapto-triazolyl derivatives of the formula (I) which can beobtained by the process according to the invention can be converted intoacid addition salts or metal salt complexes.

Suitable acids for the preparation of acid addition salts of thecompounds of the formula (I) are preferably those which have alreadybeen mentioned in connection with the description of the acid additionsalts according to the invention as being preferred acids.

The acid addition salts of the compounds of the formula (I) can beobtained in a simple manner by customary salt formation methods, forexample by dissolving a compound of the formula (I) in a suitable inertsolvent and adding the acid, for example hydrochloric acid, and they canbe isolated in a known manner, for example by filtering off, and, ifappropriate, purified by washing with an inert organic solvent.

Suitable salts for the preparation of metal salt complexes of thecompounds of the formula (I) are preferably those of metals which havealready been mentioned in connection with the description of the metalsalt complexes according to the invention as being preferred metalsalts.

The metal salt complexes of the compounds of the formula (I) can beobtained in a simple manner by customary processes, for example bydissolving the metal salt in alcohol, for example ethanol, and addingthe solution to the compounds of the formula (I). Metal salt complexescan be isolated in a known manner, for example by filtering off, and, ifappropriate, purified by recrystallization.

The active compounds according to the invention have strong microbicidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

In crop protection, fungicides are employed for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes, Deuteromycetes.

Some causative organisms of fungal and bacterial diseases which comeunder the generic names listed above may be mentioned as examples, butnot by way of limitation:

Xanthomonas species, such as Xanthomonas oryzae;

Pseudomonas species, such as Pseudomonas lachrymans;

Erwinia species, such as Erwinia amylovora;

Pythium species, such as Pythium ultimum;

Phytophthora species, such as Phytophthora infestans;

Pseudoperonospora species, such as Pseudoperonospora humuli orPseudoperonospora cubensis;

Plasmopara species, such as Plasmopara viticola;

Peronospora species, such as Peronospora pisi or P. brassicae;

Erysiphe species, such as Erysiphe graminis;

Sphaerotheca species, such as Sphaerotheca fuliginea;

Podosphaera species, such as Podosphaera leucotricha;

Venturia species, such as Venturia inaequalis;

Pyrenophora species, such as Pyrenophora teres or P. graminea;

(conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as Cochljobolus sativus;

(conidia form: [Drechslera, syn: Helminthosporium):

Uromyces species, such as Uromyces appendiculatus;

Puccinia species, such as Puccinia recondita;

Tilletia species, such as Tilletia caries;

Ustilago species, such as Ustilago nuda or Ustilago avenae;

Pellicularia species, such as Pellicularia sasakii;

Pyricularia species, such as Pyricularia oryzae;

Fusarium species, such as Fusarium culmorum;

Botrytis species, such as Botrytis cinerea;

Septoria species such as Septoria nodorum;

Leptosphaeria species, such as Leptosphaeria nodorum;

Cercospora species, such as Cercospora canescens;

Alternaria species, such as Alternaria brassicae;

Pseudocercosporella species, such as Pseudocercosporellaherpotrichoides.

The good tolerance, by plants, of the active compounds, at theconcentrations required for controlling plant diseases, permitstreatment of above-ground parts of plants, of vegetative propagationstock and seeds, and of the soil.

The active compounds according to the invention are particularlysuitable for controlling Pyricularia oryzae and Pellicularia sasakii onrice, and also for controlling cereal diseases, such asPseudocercosporella, Erysiphe species and Fusarium species. Furthermore,the substances according to the invention can also be used effectivelyagainst Venturia and Sphaerotheca. Additionally, they also have verygood in vitro activity.

In materials protection the substances of the invention can be used toprotect industrial materials against infestation and destruction byundesirable microorganisms.

The term industrial materials in the present context refers to nonlivingmaterials which have been prepared for use in industry. Examples can beindustrial materials which are to be protected by novel active compoundsagainst microbial alteration or destruction, adhesives, sizes, paper andcard, textiles, leather, wood, coating compositions and plasticsarticles, cooling lubricants and other materials which can be infestedor decomposed by microorganisms. In the context of the materials to beprotected mention may also be made of parts of production plants, forexample cooling water circuits, which may be adversely affected byreproduction of microorganisms. Preferred industrial materials in thecontext of the present invention are adhesives, sizes, papers and cards,leather, wood, coating compositions, cooling lubricants and heattransfer fluids, particularly preferably wood.

Examples of microorganisms which can bring about degradation or analteration in the industrial materials are bacteria, fungi, yeasts,algae and slime organisms. The active compounds according to theinvention preferably act against fungi, especially mould fungi,wood-discolouring and wood-destroying fungi (Basidiomycetes) and alsoagainst slime organisms and algae.

By way of example of microorganisms, mention may be made of thefollowing genera:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa,

Staphylococcus, such as Staphylococcus aureus.

Depending on their respective physical and/or chemical properties, theactive compounds can be converted into customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols, very fine capsules in polymeric substances and in coatingcompositions for seed, and also ULV cold-mist and warm-mistformulations.

These formulations are prepared in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is, emulsifying agents and/or dispersingagents, and/or foam-forming agents. If the extender used is water, it isalso possible to employ, for example, organic solvents as auxiliarysolvents. Suitable liquid solvents are essentially: aromatics, such asxylene, toluene or alkylnaphthalenes, chlorinated aromatics orchlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example mineral oil fractions, alcohols,such as butanol or glycol and also their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, and also water; by liquefied gaseous extenders orcarriers are meant liquids which are gaseous at ambient temperature andunder atmospheric pressure, for example aerosol propellants such asbutane, propane, nitrogen and carbon dioxide; as solid carriers thereare suitable: for example ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates; as solid carriers for granules there aresuitable: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, and also syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;as emulsifying and/or foam-forming agents there are suitable: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand also protein hydrolysates; as dispersing agents there are suitable:for example lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Possible furtheradditives are mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, when used in cropprotection, can be used as such or in their formulations as a mixturewith known fungicides, bactericides, acaricides, nematicides orinsecticides, for example so as to widen the spectrum of action or toprevent the build up of resistance. In many cases, synergistic effectsare obtained, i.e. the efficacy of the mixture is higher than theefficacy of the individual components.

Suitable components for the mixtures are, for example, the followingsubstances:

Fungicides:

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)-acetamide;8-hydroxyquinoline sulphate; methyl(E)-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate;methyl (E)-methoximino[alpha-(o-tolyloxy)-o-tolyl]acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,

benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate, calciumpolysulphide, captafol, captan, carbendazim, carboxin, quinomethionate,chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb,cymoxanil, cyproconazole, cyprofuram,

dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine,drazoxolon,

edifenphos, epoxyconazole, ethirimol, etridiazole,

fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet,fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazol, imazalil, imibenconazole,iminoctadine, iprobenfos (IBP), iprodione, isoprothiolane, kasugamycin,copper preparations such as: copper hydroxide, copper naphthenate,copper oxychloride, copper sulphate, copper oxide, oxine-copper andBordeaux mixture, mancopper, mancozeb, maneb, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metsulfovax, myclobutanil,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxycarboxin,

pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin,polyoxin, probenazole, prochloraz, procymidone, propamocarb,propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil,pyroquilon, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, technazene, tetraconazole, thiabendazole,thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid,triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole,tridemorph, triflumizole, triforine, triticonazole,

validamycin A, vinclozolin,

zineb, ziram.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furanecarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/acaricides/nematicides:

abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin, Bacillus thuringiensis, bendiocarb,benfuracarb, bensultap, beta-cyfluthrin, bifenthrin, BPMC, brofenprox,bromophos A, bufencarb, buprofezin, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos,chlorfluazuron chlormephos, chlorpyrifos, chlorpyrifos M,cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron,flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formnothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivermectin,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, mevinphos, mesulfenfos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A,profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate,pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum,pyridaben, pyrimidifen, pyriproxifen,

quinalphos,

RH 5992,

salithion, sebufos, silafluofen, sulfotep, sulprofos,

tebufenozid, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathen, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamidothion, XMC, xylylcarb, zetamethrin.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, is also possible.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, emulsifiable concentrates, emulsions, foams, suspensions,wettable powders, pastes, soluble powders, dusts and granules. They areused in the customary manner, for example by watering, spraying,atomizing, scattering, dusting, foaming, brushing on and the like. It isfurthermore possible to apply the active compounds by the ultra-lowvolume method or to inject the active compound formulation or the activecompound itself into the soil. The seeds of the plants can also betreated.

In the treatment of parts of plants, the concentrations of activecompound in the use forms can be varied within a relatively large range:they are in general between 1 and 0.0001% by weight, preferably between0.5 and 0.001% by weight.

In the treatment of seed, amounts of active compound of from 0.001 to 50g per kilogram of seed, preferably from 0.01 to 10 g, are generallyrequired.

In the case of the treatment of soil, active-compound concentrations offrom 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% byweight, are required at the site of action.

The compositions used for protecting industrial materials comprise theactive compounds in an amount of in general from 1 to 95%, preferablyfrom 10 to 75%.

The concentrations in which the novel active compounds are applieddepend on the nature and on the incidence of the microorganisms to becontrolled and on the composition of the material to be protected. Theoptimum amount for use can be determined by means of test series. Ingeneral, the use concentrations are in the range from 0.001 to 5% byweight, preferably from 0.05 to 1.0% by weight, based on the material tobe protected.

The effectiveness and the spectrum of action of the active compounds tobe used in materials protection in accordance with the invention and ofthe compositions, concentrates or, very generally, formulations whichcan be prepared therefrom can be increased by adding, if desired,further antimicrobially active compounds, fungicides, bactericides,herbicides, insecticides or other active compounds to increase thespectrum of action or to achieve particular effects, for exampleadditional protection against insects. These mixtures may possess abroader spectrum of action than the compounds according to theinvention.

The preparation and the use of the substances according to the inventionare illustrated by the examples below.

PREPARATION EXAMPLES Example 1 ##STR571##

At room temperature, a mixture of 1.72 g (5 mmol) of2-(1-chloro-cyclopropyl)-1(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-olin 20 ml of absolute tetrahydrofuran is admixed with stirring with 0.24g (6 mmol) of sodium hydride (60% strength in paraffin oil) and stirredfor 30 minutes. 0.72 ml (10 mmol) of acetyl chloride are then added andthe reaction mixture is stirred at room temperature for a further 4hours. The reaction mixture is then admixed with 1 ml of ethanol andconcentrated under reduced pressure. The residue that remains isextracted repeatedly with dichloromethane. The combined organic phasesare concentrated under reduced pressure. In this manner, 1.8 g (94% oftheory) of2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-acetylmercapto-1,2,4-triazol-1-yl)-propan-2-olare obtained in the form of an oil.

¹ H NMR spectrum (400 MHz; CDCl₃ ; TMS): δ=0.8-1.0 (m, 4H); 3.0 (s, 3H);3.3 (d, 1H); 3.6 (d, 1H); 4.1 (s, OH); 4.6 (d, 1H); 4.75 (d, 1H);7.2-7.55 (m, 4H); 8.5 (s, 1H) ppm.

Example 2 ##STR572##

At room temperature, a solution of 0.63 ml (5 mmol) of 4-chloro-benzoylchloride in 5 ml of absolute tetrahydrofuran is added dropwise withstirring to a mixture of 1.72 g (5 mmol) of2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol,0.69 g (5 mmol) of anhydrous potassium carbonate and 20 ml of absolutetetrahydrofuran. The reaction mixture is stirred at room temperature fora further 20 hours and then filtered off with suction and concentratedunder reduced pressure. In this manner, 2.4 g (99% of theory) of2-(1-chloro-cyclopropyl)-1(2-chlorophenyl)-3-[5-(4-chloro-benzoyl-mercapto)-1,2,4-triazol-1-yl]-propan-2-olare obtained in the form of an oil.

¹ H NMR spectrum (400 MHz; CDCl₃ ; TMS): δ=0.5-1.0 (m, 4H); 3.15 (d,1H); 3.7 (d, 1H); 4.1 (d, 1H): 5.05 (d, 11H); 7.2-8.1 (m, 8H); 8.15 (s,1H) ppm

The substances listed in the examples below are also prepared by themethods given above.

Example 3 ##STR573##

Melting point: 160° C.

Example 4 ##STR574##

¹ H NMR spectrum (400 MHz; CDCl₃ ; TMS) δ=0.5-1.0 (m, 4H), 1.35 (s, 9H),3.0 (d, 1H), 3.65 (d, 1H), 3.9 (d, 1H) 4.6 (OH), 4.9 (d, 1H), 7.2-7.55(m, 4H), 8.1 (s, 1H)

Example 5 ##STR575##

At temperatures between 0 and 5° C., first a solution of 1.28 ml (6mmol) of methyl chloroformate in 10 ml of absolute dichloromethane andthen 0.84 ml (6 mmol) of triethylamine are added dropwise with stirringto a mixture of 1.72 g (5 mmol) of2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-oland 10 ml of absolute dichloromethane. After the addition, the reactionmixture is stirred at room temperature for a further 2 hours and thendiluted with dichloromethane and washed with ice-cold aqueous sodiumcarbonate solution. The organic phase is dried over sodium sulphate andsubsequently concentrated under reduced pressure. The 1.7 g of crudeproduct that remain are chromatographed over silica gel using a mixtureof petroleum ether/ethyl acetate=1:1. Concentration of the eluate gives0.7 g (35% of theory) of2-(]-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-methoxycarbonylthio-1,2,4-triazol-1-yl)-propan-2-olin the form of an oil.

¹ H NMR spectrum (200 MHz; CDCl₃ ; TMS): δ=0.5-1.05 (m, 4H); 2.7 (s,3H); 3.1 (d, 1H); 3.6 (d, 1H); 3.9 (d, 1H): 4.7 (s, OH); 4.8 (d, 1H);7.15-7.6 (m, 4H); 7.85 (s, 1H) ppm.

The compounds listed in the examples below are also prepared by themethod given in Example 5.

Example 6 ##STR576## Melting point: 86 to 90° C. Example 7 ##STR577## MS(ci): 500 (M+H⁺) Example 8 ##STR578##

At room temperature, a solution of 0.3 ml (5 mmol) of methyl isocyanatein 5 ml of absolute tetrahydrofuran is added dropwise with stirring to amixture of 1.72 g (5 mmol) of2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol,0.1 ml of triethylamine and 20 ml of absolute tetrahydrofuran. After theaddition, the reaction mixture is stirred at room temperature for 1 hourand then concentrated under reduced pressure. The crude product thatremains is chromatographed over silica gel using a mixture of petroleumether/ethyl acetate=1:1. Concentration of the eluate gives 1.3 g (65% oftheory) of 2-(l-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-[5-(N-methyl-carbamoylthio)-1,2,4-triazol-1-yl]-propan-2-olin the form of an oil.

¹ H NMR spectrum (400 MHz; CDCl₃ ; TMS): δ=0.8-1.0 (m, 4H); 3.05 (d,3H); 3.2 (d, 1H); 3.6 (d, 1H); 3.7 (s, OH); 4.5 (d, 1H); 4.8 (d, 1H);7.2-7.55 (m, 4H); 8.6 (s, 1H); 9.9 (s, NH) ppm.

The compounds listed in the examples below are also prepared by themethod given in Example 8.

Example 9 ##STR579## Melting point: 125° C. Example 10 ##STR580## Oil

¹ H NMR spectrum (200 MHz; CDCl₃ ; TMS): δ=0.8-1.0 (m, (4H), 1.2-1.7 (m,23H), 3.2 (d, 1H), 3.4 (q, 2H), 3.6 (d, 1H), 3.7 (OH), 4.55 (d, 1H), 4.8(d, 1H), 7.2-7.55 (m, 4H), 8.1 (s, 1H), 9.9 (NH).

Example 11 ##STR581## Oil

¹ H NMR spectrum (400 MHz; CDCl₃ ; TMS): δ=0.7-1.0 (m, 4H), 1.3 (d, 6H),3.2 (d, 1H), 3.6 (d, 1H), 4.1 (m, 1H), 4.55 (d, 1H), 4.75 (d, 1H),7.15-7.6 (m, 4H), 8.6 (s, 1H), 9.9 (NH).

Example 12 ##STR582## Oil

¹ H NMR spectrum (400 MHz; CDCl₃ ; TMS): δ=0.7-1.0 (m, 4H), 3.25 (d,1H), 3.55 (OH), 3.6 (d, 1H), 4.55 (d, 1H), 4.8 (d, 1H), 7.15-7.6 (m,8H), 8.7 (s, 1H), 12.2 (NH)

Preparation of starting materials

Example 13 ##STR583## Variant α:

At -20° C., a mixture of 3.12 g (10 mmol) of2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-oland 45 ml of absolute tetrahydrofuran is admixed with 8.4 ml (21 mmol)of n-butyl-lithium in hexane and stirred at 0° C. for 30 minutes. Thereaction mixture is subsequently cooled to -70° C., admixed with 0.32 g(10 mmol) of sulphur powder and stirred at -70° C. for 30 minutes. Themixture is warmed to -10° C., admixed with ice-water and adjusted to pH5 by addition of dilute sulphuric acid. The mixture is extractedrepeatedly with ethyl acetate and the combined organic phases are driedover sodium sulphate and concentrated under reduced pressure. In thismanner, 3.2 g (93% of theory) of2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol)are obtained in the form of a solid substance which, afterrecrystallization, melts at 138-139° C.

Variant β:

With stirring, a mixture of 3.12 g (10 mmol) of2-(1-chloro-cyclopropyl)-1(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol,0.96 g (30 mmol) of sulphur powder and 20 ml of absoluteN-methyl-pyrrolidone is heated at 200° C. for 44 hours. The reactionmixture is subsequently concentrated under reduced pressure (0.2 mbar).The resulting crude product (3.1 g) is recrystallized from toluene. Inthis manner. 0.7 g (20% of=theory) of2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-olis obtained in the form of a solid substance of melting point 138-139°C.

Example 14 ##STR584##

At -70° C., a mixture of 1.41 g (5 mmol) of1,2-dichloro-4,4-dimethyl-5-fluoro-3-hydroxy-3-[(1,2,4-triazol-1-yl)-methyl]-1-penteneand 25 ml of absolute tetrahydrofuran is admixed with 4 ml (10 mmol) ofn-butyl-lithium in hexane and stirred at -70° C. for one hour. Thereaction mixture is then admixed with 0.19 g (6 mmol) of sulphur powderand stirred at -70° C. for 4 hours. The mixture is subsequentlyhydrolyzed at -70° C. by addition of 1 ml of methanol and 1 ml of aceticacid. The reaction mixture is initially diluted with ethyl acetate andthen extracted repeatedly with saturated aqueous ammonium chloridesolution. The organic phase is dried over sodium sulphate andconcentrated under reduced pressure. The resulting crude product (1.7 g)is purified by silica gel chromatography using a mixture of petroleumether and ethyl acetate 1:1 as mobile phase. In this manner, 0.5 g (32%of theory) of1,2-dichloro-4,4-dimethyl-5-fluoro-3-hydroxy-3-[(5-mercapto-12,4-triazol-1-yl)-methyl]-1-pentene is obtained in the form of a solidsubstance of melting point 162-164° C.

The compounds listed in Table 13 below are also prepared by the methodsgiven in Examples 13 and 14.

                                      TABLE 12                                    __________________________________________________________________________                                                   (II-b)                                                                          #STR585##                       -                                                                          Ex.                                                                              Comp.                                  Physical                              No. No. R.sup.2 R.sup.3 constant                                            __________________________________________________________________________    15 (II-3)                                                                            --CCl═CHCl    --C(CH.sub.3).sub.3                                                                            mp. 168-169° C.                 - 16 (II-4)                                                                                                            #STR586##                                                                     GC/MS(Cl): 376  (M+H.sup.-)                                                   - 17 (II-5)                                                                   #STR588##                                                                     mp. 163-164° C.                                                        - 18 (II-6)                                                                   --C(CH.sub.3).sub.3 mp.                                                     127° C.                         - 19 (II-7)                                                                                                            #STR591##                                                                     Oil 592##                            - 20 (II-8)                                                                                                            #STR593##                                                                     GC/MS(Cl): 340  (M+H.sup.-)                                                   - 21 (II-9)                                                                   #STR595##                                                                     GC/MS(Cl): 424  (M+H.sup.+)                                                   - 22 (II-10)                                                                  #STR597##                                                                     mp. 168° C.                   - 23 (II-11)                                                                                                           #STR599##                                                                     GC/MS(Cl): 314  (M+H.sup.+)                                                   - 24 (II-12)                                                                  #STR601##                                                                     GC/MS(Cl): 346  (M+H.sup.+)                                                   - 25 (II-13)                                                                  #STR603##                                                                     mp. 115-118° C.                                                        - 26 (II-14)                                                                  --C(CH.sub.3).sub.3 GC/MS(Cl):                                               340  (M+H.sup.+)                      - 27 (II-15)                                                                                                           #STR606##                                                                     GC/MS(Cl): 334  (M+H.sup.+)                                                   - 28 (II-16)                                                                  --C.sub.4 H.sub.9 -n *)           __________________________________________________________________________

The compound is characterized by the following signals in the ¹ H NMRspectrum (400 MHz, CDCl₃ /TMS) δ=0.8 (t, 3H); 0.85 (m, 2H); 1.25 (m,2H); 1.8 (m, 1H); 2.55 (m, 1H), 4.6 (OH); 4.9 (AB, 2H); 7.2 (dd, 1H);7.35 (d, 1H); 7.7 (s, 1H); 7.75 (d, 1H); 12.3 (5H) ppm

Example 29 ##STR609##

At -70° C., a mixture of 1.3 g (4 mmol) of3-(2-chloro-phenyl)-2-(4-fluoro-phenyl)-2-(1,2,4-triazol-1-yl-methyl)-oxirane(Z form) and 25 ml of absolute tetrahydrofuran is admixed with 2.0 ml (5mmol) of n-butyl-lithium in hexane and stirred at -70° C. for 1 hour.The reaction mixture is then admixed with 0.16 g (5 mmol) of sulphurpowder and stirred at -70° C. for 4 hours. Subsequently. 1 ml ofmethanol and 1 ml of acetic acid are simultaneously added dropwise withstirring at -70° C. The resulting mixture is diluted withdichloromethane and extracted repeatedly with saturated aqueous ammoniumchloride solution. The organic phase is dried over sodium sulphate andthen concentrated under reduced pressure. The resulting crude product(1.9 g) which, according to the gas chromatogram, contains 51.0% of thedesired product, in addition to 20.7% of starting material, isrecrystallized from toluene. In this manner, 0.8 g (55% of theory) of3-(2-chlorophenyl)-2-(4-fluoro-phenyl)-2-(5-mercapto-1,2,4-triazol-1-yl-methyl)-oxirane (Z form) is obtainedas a solid substance of melting point 179 to 180° C.

¹ H NMR spectrum (200 MHz, CDCl₃, TMS): δ=3.7 (d, J=15 Hz, 1H); 4.1 (s,1H); 5.15 (d, J=15 Hz, 1H); 6.95-7.6 (m, 8H); 7.65 (s, 1H); 11.0 (s, 1H)ppm. GC/MS (ci): 362 (M+H⁺)

Example 30 ##STR610##

At -20° C., a mixture of 1.6 g (5 mmol) of5-(4-chlorobenzyl)-2,2-dimethyl-1-(1,2,4-triazol-1-yl-methyl)-cyclopentane-1-ol(Z form) and 30 ml of absolute tetrahydrofuran is admixed with 4 ml (10mmol) of n-butyl-lithium in hexane, and stirring is continued at 0° C.for 30 minutes. The reaction mixture is subsequently cooled to -70° C.,admixed with stirring with 0.19 g (6 mmol) of sulphur powder and thenstirred at -70° C. for 1 hour and subsequently at 0° C. for 2 hours, Theresulting mixture is diluted with ethyl acetate and extracted repeatedlywith saturated aqueous ammonium chloride solution. The organic phase isdried over sodium sulphate and then concentrated under reduced pressure.The resulting crude product (2.0 g) is recrystallized from toluene. Inthis manner, 1.1 g (63% of theory) of5-(4-chloro-benzyl)-2,2-dimethyl-1-(5-mercapto-1,2,4-triazol-1-yl-methyl)-cyclopentan-1-ol(Z form) are obtained as a solid substance of melting point 179 to 180°C.

GC/MS (ci): 352 (M+H⁺)

Example 31 ##STR611##

At -20° C., a mixture of 1.59 g (5 mmol) of2-(4-chloro-benzylidene)-5,5-dimethyl-1-(1,2,4-triazol-1-yl-methyl)-cyclopentan-1-oland 30 ml of absolute tetrahydrofuran is admixed with 4.4 ml (11 mmol)of n-butyl-lithium in hexane, and stirring is continued at 0° C. for 30minutes. The reaction mixture is subsequently cooled to -70° C. admixedwith stirring with 0.19 g (6 mmol) of sulphur powder and then stirred at-20° C. for 1 hour and subsequently at 0° C. for 2 hours. The resultingmixture is diluted with ethyl acetate and extracted repeatedly withsaturated aqueous ammonium chloride solution. The organic phase is driedover sodium sulphate and then concentrated under reduced pressure. Theresulting crude product (1.9 g) is chromatographed over silica gel usingethyl acetate. In this manner, 0.8 g (46% of theory) of2-(4-chloro-benzylidene)-5,5-dimethyl-1-(5-mercapto-1,2,4-triazol-1-yl-methyl)-cyclopentan-1-olis obtained.

¹ H-NMR spectrum (200 MHz, CDCl₃ ; TMS): δ=0.9 (s,3H); 1.15 (s,3H);1.6-1.95 (m,2H); 2.4-3.0 (m,2H); 4.25 (d, 1H); 4.55 (d,1H); 5.9 (m,1H);7.1-7.3 (m, 4H); 7.6 (s, 1H) ppm

Example 32 ##STR612##

At -20° C., a mixture of 1.53 g (5 mmol) of2-(2,4-difluoro-phenyl)-1,3-bis-(1,2,4-triazol-1-yl)-propan-2-ol and 30ml of absolute tetrahydrofuran is admixed with 4.4 ml (11 mmol) ofn-butyl-lithium in hexane, and stirring is continued at 0° C. for 30minutes. The reaction mixture is subsequently cooled to -70° C. admixedwith stirring with 0.19 g (6 mmol) of sulphur powder and then stirred at-70° C. for 1 hour and subsequently at 0° C. for 2 hours. The resultingmixture is diluted with ethyl acetate and extracted repeatedly withsaturated aqueous ammonium chloride solution. The organic phase is driedover sodium sulphate and then concentrated under reduced pressure. Theresulting crude product (2.3 g) is purified by silica gel chromatographyusing a mixture of ethyl acetate and ethanol=9:1 as mobile phase. Inthis manner, 1.0 g (59% of theory) of2-(2.4-difluoro-phenyl)-1-(5-mercapto-1,2,4-triazol-1-yl)-3-(1,2,4-triazol-1-yl)-propan-2-olis obtained in the form of a solid substance of melting point 187° C.

GC/MS (ci): 339 (M+H⁺)

Example 33 ##STR613##

At -20° C., a mixture of 1.72 g (5 mmol) of2,2-dimethyl-3-hydroxy-4-(1,2,4-triazol-1-yl)-1-(4-trifluoromethoxy-phenyl)-pentaneand 30 ml of absolute tetrahydrofuran is admixed with 4.4 ml (11 mmol)of n-butyl-lithium in hexane, and stirring is continued at 0° C. for 30minutes. The reaction mixture is subsequently cooled to -70° C., admixedwith stirring with 0.19 g (6 mmol) of sulphur powder and then stirred at-70° C. for 1 hour and subsequently at 0° C. for 2 hours. The resultingmixture is diluted with ethyl acetate and extracted repeatedly withsaturated aqueous ammonium chloride solution. The organic phase is driedover sodium sulphate and then concentrated under reduced pressure. Theresulting crude product (2.2 g) is purified by silica gel chromatographyusing a mixture of petroleum ether and ethyl acetate=1:1 as mobilephase. In this manner, 1.4 g (75% of theory) of2,2-dimethyl-3-hydroxy-4-(5-mercapto-1,2,4-triazol-1-yl)-1-(4-trifluoromethoxy-phenyl)-pentaneare obtained in the form of a solid substance of melting point 125 to126° C.

GC/MS(ci): 376 (M+H⁺)

Example 34 ##STR614##

At -20° C., a mixture of 1.48 g (5 mmol) of1-(4-chloro-phenoxy)-1-(1,2,4-triazol-1-yl)-3,3-dimethyl-butan-2-ol and30 ml of absolute tetrahydrofuran is admixed with 4 ml (10 mmol) ofn-butyl-lithium, and stirring is continued at -20° C. for 30 minutes. At-20° C., the reaction mixture is then admixed with stirring with 0.19 g(6 mmol) of sulphur powder and then stirred at -20° C. for 1 hour andsubsequently at 0° C. for 2 hours. The resulting mixture is diluted withethyl acetate and extracted repeatedly with saturated aqueous ammoniumchloride solution. The organic phase is dried over sodium sulphate andthen concentrated under reduced pressure. The resulting crude product(1.9 g) is purified by silica gel chromatography using a mixture ofpetroleum ether and ethyl acetate=1:1 as mobile phase. In this manner,0.7 g (43% of theory) of1-(4-chlorophenoxy)-1-(5-mercapto-1,2,4-triazol-1-yl)-3,3-dimethyl-butan-2-ol is obtained in the form of a solid substanceof melting point 193 to 194° C.

MS(ci): 328 (M+H⁺)

Example 35 ##STR615##

With stirring, a mixture of 2.0 g (5 mmol) of2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-(1,2,4-triazol-1-yl-methyl)4-methyl-1,3-dioxolan,0.32 g (10 mmol) of sulphur powder and 10 ml of absoluteN-methylpyrrolidone is heated at 200° C. for 22 hours. The reactionmixture is subsequently concentrated under reduced pressure (0.2 mbar).The remaining residue is admixed with ethyl acetate, and the resultingmixture is extracted repeatedly with saturated aqueous ammonium chloridesolution. The organic phase is dried over sodium sulphate and thenconcentrated under reduced pressure. The resulting crude product (1.8 g)is purified by silica gel chromatography using a mixture of petroleumether and ethyl acetate=1:1 as mobile phase. In this manner, 0.9 g (41%of theory) of2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-[(5-mercapto-1,2,4-triazol-1-yl)-methyl]-4-methyl-1,3-dioxolanis obtained in the form of an isomer mixture.

MS (ci): 438 (M+H⁺, 100%)

Example 36 ##STR616##

Under an atmosphere of nitrogen and with stirring, a mixture of 142 g (5mmol) of 2-(2,4-dichloro-phenyl)-1-(1,2,4-triazol-1-yl)-pentane, 0.32 g(10 mmol) of sulphur powder and 10 ml of absolute N-methylpyrrolidone isheated at 200° C. for 3 hours. The reaction mixture is subsequentlyconcentrated under reduced pressure. The remaining residue is admixedwith ethyl acetate, and the resulting mixture is extracted repeatedlywith saturated aqueous ammonium chloride solution. The organic phase isdried over sodium sulphate and then concentrated under reduced pressure.The resulting crude product (2.1 g) is purified by silica gelchromatography using a mixture of petroleum ether and ethyl acetate=1:1as mobile phase. In this manner, 1.5 g (95% of theory) of2-(2,4-dichloro-phenyl)-1-(5-mercapto-1,2,4-triazol-1-yl)-pentane areobtained in the form of a solid substance of melting point 103° C.

Example 37 ##STR617##

Under an atmosphere of nitrogen and with stirring, a mixture of 2.93 g(10 mmol) of1-(4-chloro-phenoxy)-1-(1,2,4--triazol-1-yl)-3,3-dimethyl-butan-2-one,0.64 g (20 mmol) of sulphur powder and 10 ml of absoluteN-methylpyrrolidone is heated at 200° C. for 8 hours. The reactionmixture is subsequently concentrated under reduced pressure and, theremaining residue is dissolved in dichloromethane. The resulting mixtureis extracted repeatedly with saturated aqueous ammonium chloridesolution.

The organic phase is dried over sodium sulphate and then concentratedunder reduced pressure. The resulting crude product (2.7 g) is purifiedby silica gel chromatography using a mixture of petroleum ether andethyl acetate=1:1 as mobile phase. In this manner, 2.0 g (62% of theory)of1-(4-chlorophenoxy)-1-(5-mercapto-1,2,4-triazol-1-yl)-3,3-dimethyl-butan-2-oneare obtained in the form of a solid substance of melting point 134 to136° C.

Example 38 ##STR618##

Under an atmosphere of nitrogen and with stirring, a mixture of 1.68 g(5 mmol) of4-(4-chloro-phenyl)-2-cyano-2-phenyl-1-(1,2,4-triazol-1-yl)-butane. 0.32g (10 mmol) of sulphur powder and 10 ml of absolute N-methylpyrrolidoneis heated at 20° C. for 47 hours. The reaction mixture is subsequentlyconcentrated under reduced pressure, and the remaining residue isdissolved in ethyl acetate. The resulting mixture is extractedrepeatedly with saturated aqueous ammonium chloride solution. Theorganic phase is dried over sodium sulphate and then concentrated underreduced pressure. The resulting crude product (1.9 g) is purified bysilica gel chromatography using a mixture of petroleum ether and ethylacetate=1:1 as mobile phase. In this manner, 0.7 g (38% of theory) of4-(4-chloro-phenyl)-2-cyano-2-phenyl-1-(5-mercapto-1.2,4-triazol-1-yl)-butaneis obtained in the form of an oil.

¹ H NMR spectrum (400 MHz, CDCl₃, TMS): δ=2.4 (m, 3H); 2.75 (m, 1H); 4.5(AB, 2H); 7.0 (d. 2H); 7.2 (d, 2H); 7.4 (m, 3H); 7.55 (m, 2H); 7.8 (s,1H); 11.7 (1H) ppm.

USE EXAMPLES Example A

Pseudocercosporella herpotrichoides test/W strain; (wheat)/protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are inoculated at thebase of the stem with spores of the W strain of Pseudocercosporellaherpotrichoides.

The plants are placed in a greenhouse at a temperature of approximately10° C. and a relative atmospheric humidity of approximately 80%.

Evaluation is carried out 21 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

In this test, the compound (I-9) disclosed in Example 9 exhibits, at anapplication rate of 250 g/ha, an efficacy of 100%.

                                      TABLE A                                     __________________________________________________________________________    Pseudocercosporella herpotrichoides test/W strain; (wheat)/protective                                  Application rate of                                                                      active compound                             Active compound in g/ha Efficacy in %                                       __________________________________________________________________________    According to the invention:                                                    ##STR619##               250 100                                             __________________________________________________________________________

Example B

Erysiphe test (barley)/curative

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for curative activity, young plants are dusted with spores ofErysiphe graminis F.sp. hordei. 48 hours after the inoculation, theplants are sprayed with the preparation of active compound at the statedapplication rate.

The plants are placed in a greenhouse at a temperature of approximately20° C. and a relative atmospheric humidity of approximately 80%, topromote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

In this test, the compounds (I-1) and (I-7) disclosed in Examples 1 and7 exhibit, at an application rate of 250 g/ha, an efficacy of 100%.

                                      TABLE B                                     __________________________________________________________________________    Erysiphe test (barley)/curative                                                                         Application rate of                                    active compound                                                              Active compound in g/ha Efficacy in %                                       __________________________________________________________________________    According to the invention:                                                    ##STR620##                250 100                                               -                                                                                                     ##STR621 250 100                                   __________________________________________________________________________

Example C

Erysiphe test (barley)/protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f.sp. hordei.

The plants are placed in a greenhouse at a temperature of approximately20° C. and a relative atmospheric humidity of approximately 80%, topromote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

In this test, the compounds (I-1) and (I-7) disclosed in Examples 1 and7 exhibit, at an application rate of 250 g/ha, an efficacy of 100%.

                                      TABLE C                                     __________________________________________________________________________    Erysiphe test (barley)/protective                                                                       Application rate of                                    active compound                                                              Active compound in g/ha Efficacy in %                                       __________________________________________________________________________    According to the invention:                                                    ##STR622##                250 100                                               -                                                                                                     ##STR623 250 100                                   __________________________________________________________________________

Example D

Podosphaera test (apple)/protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of the causative organism of apple mildew Podosphaeraleucotricha. The plants are placed in a greenhouse at approximately 23°C. and a relative atmospheric humidity of approximately 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

                                      TABLE D                                     __________________________________________________________________________    Podosphaera test (apple)/protective                                                                     Application rate of                                    active compound                                                              Active compound in g/ha Efficacy in %                                       __________________________________________________________________________    According to the invention:                                                    ##STR624##                50 100                                                -                                                                                                     ##STR625 50 100                                    __________________________________________________________________________

Example E

Sphaerotheca test (cucumber)/protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Sphaerotheca fuliginea. The plants are placed in agreenhouse at approximately 23° C. and a relative atmospheric humidityof approximately 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

                                      TABLE E                                     __________________________________________________________________________    Sphaerotheca test (cucumber)/protective                                                                   Application rate of                                  active compound                                                               in g/ha Efficacy in %                                                      __________________________________________________________________________    According to the invention:                                                    ##STR626##                  50 100                                              -                                                                                                       ##STR627 50 100                                  __________________________________________________________________________

Example F

Venturia test (apple)/protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the causative organism of apple scab Venturiainaequalis and then remain in an incubation cabin at approximately 20°C. and 100% relative atmospheric humidity for 1 day.

The plants are then placed in a greenhouse at approximately 21° C. andat a relative atmospheric humidity of approximately 90%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

                                      TABLE F                                     __________________________________________________________________________    Venturia test (apple)/protective                                                                             Application rate of                               active compound                                                              Active compound in g/ha Efficacy in %                                       __________________________________________________________________________    According to the invention:                                                    ##STR628##                     50 100                                           -                                                                                                          ##STR629 50 100                                  -                                                                                                                    50 1000##                           __________________________________________________________________________

Example G

Botrytis test (bean)/protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, two small pieces of agar overgrown withBotrytis cinerea are placed onto each leaf. The inoculated plants areplaced in a dark chamber at approximately 20° C. and 100% relativeatmospheric humidity.

2 days after the inoculation, the size of the infested area on theleaves is evaluated. 0% means an efficacy which corresponds to that ofthe control, while an efficacy of 100% means that no infection isobserved.

Active compounds, active compound concentrations and test results areshown in the table below.

                  TABLE G                                                         ______________________________________                                        Botrytis test (bean)/protective                                                                           Applica-                                             tion rate                                                                     of active                                                                     compound Efficacy                                                             in g/ha in %                                                               ______________________________________                                        According to the invention:                                                    ##STR631##              500 100                                              ______________________________________                                    

What is claimed is:
 1. An acyl-mercapto-triazolyl derivative of thefollowing formula (I) ##STR632## wherein R represents straight-chain orbranched alkyl having 1 to 8 carbon atoms, straight-chain or branchedhalogenoalkyl having 1 to 6 carbon atoms and 1 to 5 identical ordifferent halogen atoms, phenyl which is unsubstituted or mono- totrisubstituted by identical or different substituents selected from thegroup consisting of halogen and alkyl having 1 to 4 carbon atoms,phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety which isunsubstituted or mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen and alkylhaving 1 to 4 carbon atoms, straight-chain or branched alkoxy having 1to 12 carbon atoms, straight-chain or branched alkylamino having 1 to 14carbon atoms or represents phenylamino which is unsubstituted or mono-to trisubstituted by identical or different substituents selected fromthe group consisting of halogen and alkyl having 1 to 4 carbon atoms,R¹represents a radical of the formula ##STR633## R² representsstraight-chain or branched alkyl having 1 to 6 carbon atoms, which isunsubstituted or mono- to tetra-substituted by identical or differentsubstituents selected from the group consisting of halogen, alkoxyhaving 1 to 4 carbon atoms, alkoximino having 1 to 4 carbon atoms in thealkoxy moiety and cycloalkyl having 3 to 7 carbon atoms, or representscycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or mono-to trisubstituted by identical or different substituents selected fromthe group consisting of halogen, cyano and alkyl having 1 to 4 carbonatoms, or represents aralkyl having 6 to 10 carbon atoms in the arylmoiety and 1 to 4 carbon atoms in the straight-chain or branched alkylmoiety, wherein each of the aryl moieties is unsubstituted or mono- totrisubstituted by identical or different substituents selected from thegroup consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxyhaving 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenalkyl having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkoxy having 1 to 2 carbon atoms and 1to 5 identical or different halogen atoms, halogenoalkylthio having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonylhaving 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety, nitro and cyano, or represents aroxyalkyl having 6 to 10carbon atoms in the aryl moiety and 1 to 4 carbon atoms in thestraight-chain or branched oxyalkyl moiety, wherein each of the arylmoieties is unsubstituted or mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen,alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms,alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbonatoms and 1 to 5 identical or different halogen atoms, halogenoalkoxyhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identicalor different halogen atoms, cycloalkyl having 3 to 7 carbon atoms,phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxymoiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moietyand 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano, orrepresents aryl having 6 to 10 carbon atoms, wherein each of theseradicals is unsubstituted or mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen,alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms,alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbonatoms and 1 to 5 identical or different halogen atoms, halogenoalkoxyhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identicalor different halogen atoms, cycloalkyl having 3 to 7 carbon atoms,phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxymoiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moietyand 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano, and R³represents straight-chain or branched alkyl having 1 to 6 carbon atoms,which is unsubstituted or mono- to tetra-substituted by identical ordifferent substituents selected from the group consisting of halogen,alkoxy having 1 to 4 carbon atoms, alkoximino having 1 to 4 carbon atomsin the alkoxy moiety and cycloalkyl having 3 to 7 carbon atoms, orrepresents cycloalkyl having 3 to 7 carbon atoms, which is unsubstitutedor mono- to trisubstituted by identical or different substituentsselected from the group consisting of halogen, cyano and alkyl having 1to 4 carbon atoms, or represents aralkyl having 6 to 10 carbon atoms inthe aryl moiety and 1 to 4 carbon atoms in the straight-chain orbranched alkyl moiety, wherein each of the aryl moieties isunsubstituted or mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen, alkyl having1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms, halogenoalkoxy having 1 or 2carbon atoms, and 1 to 5 identical or different halogen atoms,halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl,phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety,alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to4 carbon atoms in the alkyl moiety, nitro and cyano, or representsaroxyalkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 4carbon atoms in the straight-chain or branched oxyalkyl moiety, whereineach of the aryl moieties is unsubstituted or mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand cyano, or represents aryl having 6 to 10 carbon atoms, which isunsubstituted or mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen, alkyl having1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms, halogenoalkoxy having 1 or 2carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl,phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety,alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to4 carbon atoms in the alkyl moiety, nitro and cyano.
 2. A microbicidalcomposition comprising a microbicidally effective amount of a compoundas claimed in claim 1 and an inert diluent.
 3. A method for controllingundesired microorganisms in plant protection and in the preservation ofmaterials, which method comprises applying to such undesiredmicroorganisms or to their habitat a microbicidally effective amount ofa compound as claimed in claim
 1. 4. An acyl-mercapto-triazolylderivative of the following formula ##STR634##